NO127919B - - Google Patents

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Info

Publication number: NO127919B
Authority: NO; Norway
Prior art keywords: benzyl; tetrahydropyridine; hexahydro; formula; solution
Prior art date: 1967-09-25

Application number

NO314268A

Other languages

English (en)

Norwegian (no)

Inventor

N Albertson

W Wetterau

Original Assignee

Sterling Drug Inc

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.)

1967-09-25

Filing date

1968-08-09

Publication date

1973-09-03

1968-08-09 Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc

1973-09-03 Publication of NO127919B publication Critical patent/NO127919B/no

Links

MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 17
238000000034 method Methods 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
238000010438 heat treatment Methods 0.000 claims description 7
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
239000012279 sodium borohydride Substances 0.000 claims description 6
238000003747 Grignard reaction Methods 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
239000002841 Lewis acid Substances 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
150000007517 lewis acids Chemical class 0.000 claims description 4
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical class C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 3
230000001476 alcoholic effect Effects 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
238000007363 ring formation reaction Methods 0.000 claims description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
239000000243 solution Substances 0.000 description 31
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000007787 solid Substances 0.000 description 15
-1 methoxy, ethoxy Chemical group 0.000 description 13
239000000047 product Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 8
239000000706 filtrate Substances 0.000 description 7
239000012458 free base Substances 0.000 description 7
239000011777 magnesium Substances 0.000 description 7
229910052749 magnesium Inorganic materials 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
239000003921 oil Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YXFZCACEHYCPHA-UHFFFAOYSA-N 1,2-dibenzyl-3,4-dimethyl-2H-pyridine Chemical compound C(C1=CC=CC=C1)N1C(C(=C(C=C1)C)C)CC1=CC=CC=C1 YXFZCACEHYCPHA-UHFFFAOYSA-N 0.000 description 2
OQKHDOZOAIDXNV-UHFFFAOYSA-N 1,6-dibenzyl-4,5-dimethyl-3,6-dihydro-2h-pyridine Chemical compound C=1C=CC=CC=1CN1CCC(C)=C(C)C1CC1=CC=CC=C1 OQKHDOZOAIDXNV-UHFFFAOYSA-N 0.000 description 2
SPGJRQAEUMRKOO-UHFFFAOYSA-M 1-benzyl-3,4-dimethylpyridin-1-ium iodide Chemical compound [I-].C(C1=CC=CC=C1)[N+]1=CC(=C(C=C1)C)C SPGJRQAEUMRKOO-UHFFFAOYSA-M 0.000 description 2
OWVMQHCIDREXSX-UHFFFAOYSA-M 1-benzyl-3,4-dimethylpyridin-1-ium;bromide Chemical compound [Br-].C1=C(C)C(C)=CC=[N+]1CC1=CC=CC=C1 OWVMQHCIDREXSX-UHFFFAOYSA-M 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000007818 Grignard reagent Substances 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
229940035676 analgesics Drugs 0.000 description 2
239000000730 antalgic agent Substances 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000010520 demethylation reaction Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
150000004795 grignard reagents Chemical class 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
239000000155 melt Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
150000003891 oxalate salts Chemical class 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
238000005303 weighing Methods 0.000 description 2
AOCXXQNURLBPMB-UHFFFAOYSA-N 1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-triene Chemical compound C1C2=CC=CC=C2C2(C)C(C)C1NCC2 AOCXXQNURLBPMB-UHFFFAOYSA-N 0.000 description 1
ZDZRSXDYPGEIBS-UHFFFAOYSA-N 1,6-dibenzyl-4,5-dimethyl-3,6-dihydro-2h-pyridine;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=CC=CC=1CN1CCC(C)=C(C)C1CC1=CC=CC=C1 ZDZRSXDYPGEIBS-UHFFFAOYSA-N 0.000 description 1
KSKPCURZYVZTBP-UHFFFAOYSA-N 1-benzyl-2-[(4-methoxyphenyl)methyl]-3,4-dimethyl-2h-pyridine Chemical group C1=CC(OC)=CC=C1CC1C(C)=C(C)C=CN1CC1=CC=CC=C1 KSKPCURZYVZTBP-UHFFFAOYSA-N 0.000 description 1
CWNOHDOVDQQNRN-UHFFFAOYSA-N 1-benzyl-3,4-dimethyl-2H-pyridine Chemical compound C(C1=CC=CC=C1)N1CC(=C(C=C1)C)C CWNOHDOVDQQNRN-UHFFFAOYSA-N 0.000 description 1
LQJZTXYKZKEWHV-UHFFFAOYSA-N 1-benzyl-4,5-dimethyl-3,6-dihydro-2H-pyridine oxalic acid Chemical compound C(C(=O)O)(=O)O.C(C1=CC=CC=C1)N1CC(=C(CC1)C)C LQJZTXYKZKEWHV-UHFFFAOYSA-N 0.000 description 1
SICFQRREHHVVBL-UHFFFAOYSA-N 1-benzyl-4-ethyl-3-methyl-2H-pyridine Chemical compound C(C1=CC=CC=C1)N1CC(=C(C=C1)CC)C SICFQRREHHVVBL-UHFFFAOYSA-N 0.000 description 1
FHGJMCCUVVAWNM-UHFFFAOYSA-M 1-benzyl-4-ethyl-3-methylpyridin-1-ium;iodide Chemical compound [I-].C1=C(C)C(CC)=CC=[N+]1CC1=CC=CC=C1 FHGJMCCUVVAWNM-UHFFFAOYSA-M 0.000 description 1
FGVXHUJLIAKCEK-UHFFFAOYSA-N 1-benzyl-6-[(4-methoxyphenyl)methyl]-4,5-dimethyl-3,6-dihydro-2h-pyridine Chemical compound C1=CC(OC)=CC=C1CC1C(C)=C(C)CCN1CC1=CC=CC=C1 FGVXHUJLIAKCEK-UHFFFAOYSA-N 0.000 description 1
RPMPAQXGZYLEST-UHFFFAOYSA-N 3-benzyl-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol Chemical compound CC1C2CC3=CC=C(O)C=C3C1(C)CCN2CC1=CC=CC=C1 RPMPAQXGZYLEST-UHFFFAOYSA-N 0.000 description 1
FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
230000020335 dealkylation Effects 0.000 description 1
238000006900 dealkylation reaction Methods 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000004694 iodide salts Chemical group 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
DXESFJJJWBHLJX-UHFFFAOYSA-N norcyclazocine Chemical compound C1C2=CC=C(O)C=C2C2(C)C(C)C1NCC2 DXESFJJJWBHLJX-UHFFFAOYSA-N 0.000 description 1
GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229960000482 pethidine Drugs 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
239000012450 pharmaceutical intermediate Substances 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1

Landscapes

Hydrogenated Pyridines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Other In-Based Heterocyclic Compounds (AREA)

NO314268A 1967-09-25 1968-08-09 NO127919B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US67039167A	1967-09-25	1967-09-25

Publications (1)

Publication Number	Publication Date
NO127919B true NO127919B (de)	1973-09-03

Family

ID=24690222

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO314268A NO127919B (de)	1967-09-25	1968-08-09

Country Status (4)

Country	Link
JP (2)	JPS4833751B1 (de)
AT (1)	AT285615B (de)
IL (1)	IL30338A (de)
NO (1)	NO127919B (de)

1968
- 1968-07-09 IL IL30338A patent/IL30338A/xx unknown
- 1968-07-24 AT AT717468A patent/AT285615B/de not_active IP Right Cessation
- 1968-08-09 NO NO314268A patent/NO127919B/no unknown
1971
- 1971-11-09 JP JP8874471A patent/JPS4833751B1/ja active Pending
- 1971-11-09 JP JP8874571A patent/JPS5317596B1/ja active Pending

Also Published As

Publication number	Publication date
JPS5317596B1 (de)	1978-06-09
JPS4833751B1 (de)	1973-10-16
IL30338A0 (en)	1968-09-26
AT285615B (de)	1970-11-10
IL30338A (en)	1972-10-29

Publication	Publication Date	Title
Boekelheide et al.	1952	Reissert Compounds. Further Alkylation Studies and a Novel Rearrangement1
Bailey et al.	1948	The Mannich Reaction with 1, 2-Dibenzoylethane1, 2
IL25213A (en)	1970-01-29	4-hydroxy-piperidine derivatives and their preparation
NO127919B (de)	1973-09-03
IL29467A (en)	1973-01-30	N-phenyl indoline derivatives
US3225031A (en)	1965-12-21	Phenyl-benzazepines and methods for their manufacture
US2906757A (en)	1959-09-29	Their preparation
EP0077536B1 (de)	1986-07-16	2'-Substituierte-spiro(benzofuran-2(3H),1'-cycloalkane), ein Verfahren zu ihrer Herstellung, sie enthaltende pharmazeutische Zusammenstellungen und ihre Anwendung als Arzneimittel
SU1301311A3 (ru)	1987-03-30	Способ получени производных гексагидроазепина или пиперидина, или пирролидина (его варианты)
US3037986A (en)	1962-06-05	2-(para-methoxyphenylcarbinol)-1-(phenylalkyl) piperidinium hydrobromide
CA1148150A (en)	1983-06-14	Phenylmorphans, intermediates and method of preparation
IL29340A (en)	1972-02-29	Dibenzoazepine derivatives and their preparation
IL36239A (en)	1971-06-23	4-hydroxy-4-) 2-oxo-3-tetrahydroporil (piperidine and its preparation
US3644373A (en)	1972-02-22	Method for the production of 3-substituted-1 2 3 4 5 6-hexahydro-6 11-dimethyl-8-hydroxy-2 6-methano-3-benzazocines
Greer et al.	1955	The Beckmann rearrangement. VII. The isolation and rearrangement of 2, 4, 6-trimethylacetophenone oxime
US3006925A (en)	1961-10-31	J-pyrrolidyl ethanols
US3876644A (en)	1975-04-08	Process for the production of 6,7-benzomorphanes
TW294666B (de)	1997-01-01
US3678056A (en)	1972-07-18	Process for the preparation of 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines
King et al.	1946	The preparation and properties of some β-aminopropionic acid derivatives
Kisaki et al.	1960	Chemistry of the N′-Oxides of Nicotine and Myosmine
DE1810341A1 (de)	1969-08-07	Verfahren zur Herstellung von Tetrahydroisochinolin-Derivaten
ROSE et al.	1958	Rearrangement and Condensation of Reissert Compounds with Grignard Reagents. III
US3313822A (en)	1967-04-11	Diphenyl substituted aminoalkyl pyridines
NO137695B (no)	1977-12-27	Analogifremgangsm}te for fremstilling av terapeutisk aktive n-tienylmetyl-heterocykliske forbindelser