CA1110642A - Process for the preparation of o-alkylated hydroxylamines - Google Patents

Process for the preparation of o-alkylated hydroxylamines

Info

Publication number: CA1110642A
Authority: CA; Canada
Prior art keywords: group; formula; carbon atoms; hydrogen; alkyl
Prior art date: 1978-05-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA326,980A

Other languages

English (en)

French (fr)

Inventor

Ulrich Gebert

Werner Thorwart

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-05-08

Filing date

1979-05-04

Publication date

1981-10-13

1979-05-04 Application filed by Hoechst AG filed Critical Hoechst AG

1981-10-13 Application granted granted Critical

1981-10-13 Publication of CA1110642A publication Critical patent/CA1110642A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 22
238000002360 preparation method Methods 0.000 title claims abstract description 16
150000002443 hydroxylamines Chemical class 0.000 title claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 35
150000001875 compounds Chemical class 0.000 claims abstract description 30
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 30
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
-1 hydroxyl-amine compound Chemical class 0.000 claims abstract description 26
239000001257 hydrogen Substances 0.000 claims abstract description 23
125000003118 aryl group Chemical group 0.000 claims abstract description 22
239000002253 acid Substances 0.000 claims abstract description 20
125000005843 halogen group Chemical group 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 19
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
239000012458 free base Substances 0.000 claims abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
230000007062 hydrolysis Effects 0.000 claims abstract description 5
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 5
229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
125000005842 heteroatom Chemical group 0.000 claims abstract description 4
231100000252 nontoxic Toxicity 0.000 claims abstract description 4
230000003000 nontoxic effect Effects 0.000 claims abstract description 4
125000006239 protecting group Chemical group 0.000 claims abstract description 4
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003277 amino group Chemical group 0.000 claims abstract description 3
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
150000003254 radicals Chemical class 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract 2
150000007522 mineralic acids Chemical class 0.000 claims abstract 2
150000007524 organic acids Chemical class 0.000 claims abstract 2
125000004432 carbon atom Chemical group C* 0.000 claims description 41
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 9
125000001188 haloalkyl group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 claims description 3
150000005840 aryl radicals Chemical class 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
230000000269 nucleophilic effect Effects 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
239000005864 Sulphur Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 3
229960000443 hydrochloric acid Drugs 0.000 claims 2
235000011167 hydrochloric acid Nutrition 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
OCXUZXFYKMTQNS-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-(oxiran-2-ylmethyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CC2OC2)CC1 OCXUZXFYKMTQNS-UHFFFAOYSA-N 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 3
150000002367 halogens Chemical class 0.000 abstract 1
125000003107 substituted aryl group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
150000002924 oxiranes Chemical class 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
239000002585 base Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
229960004132 diethyl ether Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
150000002989 phenols Chemical class 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
150000003573 thiols Chemical class 0.000 description 3
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
238000003780 insertion Methods 0.000 description 2
230000037431 insertion Effects 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
VTWKXBJHBHYJBI-SOFGYWHQSA-N (ne)-n-benzylidenehydroxylamine Chemical compound O\N=C\C1=CC=CC=C1 VTWKXBJHBHYJBI-SOFGYWHQSA-N 0.000 description 1
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 1
KJPJBSQPYWKEJR-UHFFFAOYSA-N CCCOS(=O)(=O)C1=C2OC2=CC=C1 Chemical compound CCCOS(=O)(=O)C1=C2OC2=CC=C1 KJPJBSQPYWKEJR-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical group C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000219 Sympatholytic Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000007098 aminolysis reaction Methods 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
230000000507 anthelmentic effect Effects 0.000 description 1
230000002082 anti-convulsion Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000001857 anti-mycotic effect Effects 0.000 description 1
230000001741 anti-phlogistic effect Effects 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
ZAYITQDIKSBHDD-UHFFFAOYSA-N benzene methane Chemical compound C.C1=CC=CC=C1.C1=CC=CC=C1 ZAYITQDIKSBHDD-UHFFFAOYSA-N 0.000 description 1
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
239000012964 benzotriazole Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000001913 cellulose Chemical class 0.000 description 1
229920002678 cellulose Chemical class 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
239000006196 drop Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229940052303 ethers for general anesthesia Drugs 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229940028332 halog Drugs 0.000 description 1
JKXCZYCVHPKTPK-UHFFFAOYSA-N hydrate;trihydrochloride Chemical compound O.Cl.Cl.Cl JKXCZYCVHPKTPK-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
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229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001603 reducing effect Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
230000000894 saliuretic effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008107 starch Chemical class 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
230000000948 sympatholitic effect Effects 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
239000003826 tablet Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

CA326,980A 1978-05-08 1979-05-04 Process for the preparation of o-alkylated hydroxylamines Expired CA1110642A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP2820013.7		1978-05-08
DE19782820013 DE2820013A1 (de)	1978-05-08	1978-05-08	Verfahren zur herstellung von o-alkylierten hydroxylaminen

Publications (1)

Publication Number	Publication Date
CA1110642A true CA1110642A (en)	1981-10-13

Family

ID=6038858

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA326,980A Expired CA1110642A (en)	1978-05-08	1979-05-04	Process for the preparation of o-alkylated hydroxylamines

Country Status (9)

Country	Link
AT (1)	AT374448B (de)
CA (1)	CA1110642A (de)
CH (1)	CH647497A5 (de)
DE (1)	DE2820013A1 (de)
DK (1)	DK188379A (de)
ES (1)	ES480294A2 (de)
FI (1)	FI791453A7 (de)
HU (1)	HU179985B (de)
SE (1)	SE7903970L (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2651083A1 (de) *	1976-11-09	1978-05-18	Hoechst Ag	Neue o-alkylierte hydroxylamine, verfahren zu ihrer herstellung und ihre verwendung
US5393921A (en) *	1993-07-07	1995-02-28	The Gillette Company	Process for synthesizing O-substituted oxime compounds and conversion to the corresponding O-substituted hydroxylamine
US8062995B2 (en)	2005-09-15	2011-11-22	Bayer Cropscience Ag	Dioxazine-substituted arylamides

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3565398D1 (en) *	1984-04-12	1988-11-10	Allied Signal Inc	Process for the synthesis of o-substituted oxime compounds and the conversion thereof into the corresponding hydroxylamine o-substituted

1978
- 1978-05-08 DE DE19782820013 patent/DE2820013A1/de not_active Withdrawn
1979
- 1979-05-04 CA CA326,980A patent/CA1110642A/en not_active Expired
- 1979-05-07 FI FI791453A patent/FI791453A7/fi not_active Application Discontinuation
- 1979-05-07 ES ES480294A patent/ES480294A2/es not_active Expired
- 1979-05-07 DK DK188379A patent/DK188379A/da not_active Application Discontinuation
- 1979-05-07 SE SE7903970A patent/SE7903970L/xx not_active Application Discontinuation
- 1979-05-07 AT AT0340679A patent/AT374448B/de not_active IP Right Cessation
- 1979-05-07 HU HU79HO2148A patent/HU179985B/hu unknown
- 1979-05-07 CH CH4231/79A patent/CH647497A5/de not_active IP Right Cessation

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2651083A1 (de) *	1976-11-09	1978-05-18	Hoechst Ag	Neue o-alkylierte hydroxylamine, verfahren zu ihrer herstellung und ihre verwendung
US5393921A (en) *	1993-07-07	1995-02-28	The Gillette Company	Process for synthesizing O-substituted oxime compounds and conversion to the corresponding O-substituted hydroxylamine
US8062995B2 (en)	2005-09-15	2011-11-22	Bayer Cropscience Ag	Dioxazine-substituted arylamides
US8486934B2 (en)	2005-09-15	2013-07-16	Bayer Cropscience Ag	Oxadiazine-substituted arylamides

Also Published As

Publication number	Publication date
ES480294A2 (es)	1979-12-01
FI791453A7 (fi)	1981-01-01
DK188379A (da)	1979-11-09
HU179985B (en)	1983-01-28
CH647497A5 (en)	1985-01-31
ATA340679A (de)	1983-09-15
SE7903970L (sv)	1979-11-09
AT374448B (de)	1984-04-25
DE2820013A1 (de)	1979-11-22

Legal Events

Date	Code	Title	Description
1998-10-13	MKEX	Expiry

Publication	Publication Date	Title
DE69835430T2 (de)	2007-03-08	Sulfonamidderivate, ihre herstellung und verwendung
KR970009728B1 (ko)	1997-06-17	2-[2-[4-[(4-클로로페닐)페닐메틸]-1-피페라지닐]에톡시]-아세트산 및 그의 중염산염의 제조방법
WO1997015567A1 (de)	1997-05-01	5-gliedrige heterocyclen, diese verbindungen enthaltende arzneimittel und deren verwendung sowie verfahren zu ihrer herstellung
CA1072562A (en)	1980-02-26	1-substituted-4-benzylidenepiperidines
NO155805B (no)	1987-02-23	Analogifremgangsmaate for fremstilling av terapeutisk virksomme 2-(4-(difenylmethyl)-1-piperazinyl)-eddiksyrer og deres amider og ikke-toksiske salter.
NO316753B1 (no)	2004-04-26	Substituerte aza- og diazacykloheptan og -cyklooktan-forbindelser og deres anvendelser, samt farmasoytiske blandinger inneholdende slike forbindelser
CA2165922A1 (en)	1996-06-24	Piperazine derivatives, medicaments comprising these compounds, their use and processes for their preparation
US4404384A (en)	1983-09-13	O-[3-(4-Substituted-piperazin-1-yl)-2-hydroxypropyl]-hydroxylamines
US6255327B1 (en)	2001-07-03	Diphenyl-substituted heterocycles, processes for preparing them and their use as pharmaceutical compositions
US4891378A (en)	1990-01-02	Nortropanyl containing pyrrolidinones, pharmaceutical compositions and use
US3364220A (en)	1968-01-16	Heterocyclicaminoalkylguanidines
US4032559A (en)	1977-06-28	N,2-dicyanoacetimidates
US3051707A (en)	1962-08-28	Unsymmetrical mono-(aminoalkylene)-hydrazines
DE3742716A1 (de)	1989-06-22	Imidazolderivate ii
Howard et al.	1953	Piperazines. II. 1-Heterocyclicpiperazines and 1-Hetero-Cyclic-4-Carbethoxypiperazines
GB1575904A (en)	1980-10-01	Phenyl piperazines
EP0213326B1 (de)	1991-03-06	2,5-Dimethylpyrrolderivative, ihre Herstellung und ihre Verwendung
US3284453A (en)	1966-11-08	4-(2-aroylethyl)-1-piperazinecarboxylic acid esters
HU191869B (en)	1987-04-28	Process for producing new nicotinamide-1-oxide derivatives of histamine h-2 receptor-blocking activity and pharmaceutical compositions containing them
US4659721A (en)	1987-04-21	Alkanol derivatives, and pharmaceutical preparation containing these compounds
US4166852A (en)	1979-09-04	Piperazino-pyrimidines and their use as spasmolytic agents
CH647497A5 (en)	1985-01-31	Process for the preparation of O-substituted hydroxylamines
US4118501A (en)	1978-10-03	Thiazolidine derivatives
SE435507B (sv)	1984-10-01	Forfarande for framstellning av trimetoxifenoxi-propyl-piperezinderivat
US4851410A (en)	1989-07-25	1,4-disubstituted pyrazole derivatives, compositions and use