CH442358A - Verfahren zur Herstellung veresterter Aminoalkohole - Google Patents

Verfahren zur Herstellung veresterter Aminoalkohole

Info

Publication number: CH442358A
Authority: CH; Switzerland
Prior art keywords: ether; formula; compound; reaction; calculated
Prior art date: 1960-10-22

Application number

CH1208361A

Other languages

German (de)

English (en)

Inventor

Kralt Teunis

Adriaan Peperkamp Hendrik

Original Assignee

Philips Nv

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.)

1960-10-22

Filing date

1961-10-19

Publication date

1967-08-31

1961-10-19 Application filed by Philips Nv filed Critical Philips Nv

1967-08-31 Publication of CH442358A publication Critical patent/CH442358A/de

Links

238000000034 method Methods 0.000 title claims description 12
150000001414 amino alcohols Chemical class 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
230000001419 dependent effect Effects 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 38
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 15
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 11
239000007788 liquid Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
150000003974 aralkylamines Chemical class 0.000 description 6
150000002497 iodine compounds Chemical class 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
238000003860 storage Methods 0.000 description 6
KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
238000001914 filtration Methods 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000011734 sodium Substances 0.000 description 5
235000009518 sodium iodide Nutrition 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000002253 acid Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
150000001805 chlorine compounds Chemical class 0.000 description 4
-1 chlorine-bromine compounds 4-chloro-butanol esters Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000005406 washing Methods 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
235000020075 ouzo Nutrition 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
VFEXSRRSZSHURZ-UHFFFAOYSA-N N-ethyl-4-methoxy-N-propan-2-ylaniline Chemical compound C(C)N(C(C)C)C1=CC=C(C=C1)OC VFEXSRRSZSHURZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
QAMJKWRBXRPCIQ-UHFFFAOYSA-M sodium;3,4-dimethoxybenzoate Chemical compound [Na+].COC1=CC=C(C([O-])=O)C=C1OC QAMJKWRBXRPCIQ-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 description 1
WFWKNGZODAOLEO-UHFFFAOYSA-N 1-(4-Methoxyphenyl)-2-propanone Chemical compound COC1=CC=C(CC(C)=O)C=C1 WFWKNGZODAOLEO-UHFFFAOYSA-N 0.000 description 1
SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 1
DAUAQNGYDSHRET-UHFFFAOYSA-M 3,4-dimethoxybenzoate Chemical compound COC1=CC=C(C([O-])=O)C=C1OC DAUAQNGYDSHRET-UHFFFAOYSA-M 0.000 description 1
DAUAQNGYDSHRET-UHFFFAOYSA-N 3,4-dimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1OC DAUAQNGYDSHRET-UHFFFAOYSA-N 0.000 description 1
ANNLKRCYKOMMMX-UHFFFAOYSA-N COC(C(CCCCBr)=CC(C(O)=O)=C1OC)=C1OC Chemical compound COC(C(CCCCBr)=CC(C(O)=O)=C1OC)=C1OC ANNLKRCYKOMMMX-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910010082 LiAlH Inorganic materials 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
GPVDHNVGGIAOQT-UHFFFAOYSA-N Veratric acid Natural products COC1=CC=C(C(O)=O)C(OC)=C1 GPVDHNVGGIAOQT-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 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
150000001649 bromium compounds Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
238000000605 extraction Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000005245 sintering Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
BIGQPYZPEWAPBG-UHFFFAOYSA-N veratric acid methyl ester Natural products COC(=O)C1=CC=C(OC)C(OC)=C1 BIGQPYZPEWAPBG-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1208361A 1960-10-22 1961-10-19 Verfahren zur Herstellung veresterter Aminoalkohole CH442358A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL257148		1960-10-22

Publications (1)

Publication Number	Publication Date
CH442358A true CH442358A (de)	1967-08-31

Family

ID=19752652

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1208361A CH442358A (de)	1960-10-22	1961-10-19	Verfahren zur Herstellung veresterter Aminoalkohole

Country Status (4)

Country	Link
BE (1)	BE609490A (fr)
CH (1)	CH442358A (fr)
ES (1)	ES271353A1 (fr)
GB (1)	GB1009082A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN119431161B (zh) *	2024-11-28	2025-09-19	河北广祥制药有限公司	一种盐酸美贝维林的合成方法

1961
- 1961-10-19 ES ES0271353A patent/ES271353A1/es not_active Expired
- 1961-10-19 GB GB3752961A patent/GB1009082A/en not_active Expired
- 1961-10-19 CH CH1208361A patent/CH442358A/de unknown
- 1961-10-23 BE BE609490A patent/BE609490A/fr unknown

Also Published As

Publication number	Publication date
ES271353A1 (es)	1962-03-01
GB1009082A (en)	1965-11-03
BE609490A (fr)	1962-04-15

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