JPS5681560A - Preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1- propanol and its addition salt - Google Patents

Preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1- propanol and its addition salt

Info

Publication number
JPS5681560A
JPS5681560A JP15811279A JP15811279A JPS5681560A JP S5681560 A JPS5681560 A JP S5681560A JP 15811279 A JP15811279 A JP 15811279A JP 15811279 A JP15811279 A JP 15811279A JP S5681560 A JPS5681560 A JP S5681560A
Authority
JP
Japan
Prior art keywords
benzylpiperidino
hydroxyphenyl
propanol
hydroxypropiophenone
brominating
Prior art date
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.)
Granted
Application number
JP15811279A
Other languages
Japanese (ja)
Other versions
JPS6239153B2 (en
Inventor
Bonpei Yasui
Tomohisa Miyamoto
Katsuyuki Hiraoka
Yoshitaka Sako
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.)
FUNAI CORP
Funai Pharmaceutical Industries Ltd
Original Assignee
FUNAI CORP
Funai Pharmaceutical Industries Ltd
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.)
Filing date
Publication date
Application filed by FUNAI CORP, Funai Pharmaceutical Industries Ltd filed Critical FUNAI CORP
Priority to JP15811279A priority Critical patent/JPS5681560A/en
Priority to GB8038771A priority patent/GB2067187B/en
Priority to PH24937A priority patent/PH16735A/en
Priority to CA000366167A priority patent/CA1141387A/en
Priority to US06/213,033 priority patent/US4377691A/en
Priority to IT26487/80A priority patent/IT1148744B/en
Priority to AR283504A priority patent/AR229157A1/en
Priority to DE19803045916 priority patent/DE3045916A1/en
Priority to ES497527A priority patent/ES497527A0/en
Priority to FR8025923A priority patent/FR2471374A1/en
Priority to CH9032/80A priority patent/CH648550A5/en
Priority to BR8008020A priority patent/BR8008020A/en
Priority to AT0597580A priority patent/AT374181B/en
Publication of JPS5681560A publication Critical patent/JPS5681560A/en
Priority to HK71984A priority patent/HK71984A/en
Publication of JPS6239153B2 publication Critical patent/JPS6239153B2/ja
Granted legal-status Critical Current

Links

Landscapes

  • Hydrogenated Pyridines (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

PURPOSE: To prepare the titled compound useful as a remedy for sequela of cerebral lesion, in one reactor, by brominating 4-hydroxypropiophenone without benzylation step, removing by-produced HBR with inert gas stream, and subjecting the product successively to condensation and reduction reactions.
CONSTITUTION: 1-(4-Hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol (hereafter called ifenprodil)is prepared by (1) brominating 4-hydroxypropiophenone in a solvent such as methanol, ethanol, and ethers, (2) removing the by-produced HBr from the reaction mixture by passing inert gas thereto, (3) heating the product under reflux in the presence of 4-benzylpyridine in methanol or ether as a solvent, (4) heating the resulting reaction mixture in the presence of a catalytic reduction catalyst (e.g. Pd-C) under pressure, and (5) hydrolyzing the infenprodil hydrobromide thus obtained.
COPYRIGHT: (C)1981,JPO&Japio
JP15811279A 1979-12-07 1979-12-07 Preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1- propanol and its addition salt Granted JPS5681560A (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
JP15811279A JPS5681560A (en) 1979-12-07 1979-12-07 Preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1- propanol and its addition salt
GB8038771A GB2067187B (en) 1979-12-07 1980-12-03 Process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol and acid addition salts thereof
PH24937A PH16735A (en) 1979-12-07 1980-12-03 A new process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol and acid addition salts thereof
CA000366167A CA1141387A (en) 1979-12-07 1980-12-04 Process for the preparation of 1-(4-hydroxyphenyl)-2- (4-benzylpiperidino)-1-propanol and acid-addition salts thereof
US06/213,033 US4377691A (en) 1979-12-07 1980-12-04 Process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol and acid-addition salts thereof
DE19803045916 DE3045916A1 (en) 1979-12-07 1980-12-05 METHOD FOR PRODUCING 4-BENZYL- (ALPHA) - (P-HYDROXYPHENYL) - (BETA) -METHYL-1-PIPERIDINAETHANOL AND ITS SALTS WITH ACIDS
AR283504A AR229157A1 (en) 1979-12-07 1980-12-05 PROCEDURE FOR THE PREPARATION OF 1- (4-HYDROXIPHENYL) -2- (4-BENCILPIPERIDINE) -1-PROPANOL
IT26487/80A IT1148744B (en) 1979-12-07 1980-12-05 PROCESS FOR THE PREPARATION OF 1- (4-HYDROXYPHENYL) -2- (4-BENZYLPIPERIDINE) -1-PROPANOL AND ITS ADDITION SALTS WITH ACID
ES497527A ES497527A0 (en) 1979-12-07 1980-12-05 A PROCEDURE FOR THE PREPARATION OF 1- (4-HYDROXIPHENYL) - 2- (4-BENZYLPIPERIDINE) -1-PROPANOL
FR8025923A FR2471374A1 (en) 1979-12-07 1980-12-05 NOVEL PROCESS FOR THE PREPARATION OF 1- (4-HYDROXYPHENYL) -2- (4-BENZYLPIPERIDINO) -PROPANOL AND ITS ACID ADDITION SALTS
CH9032/80A CH648550A5 (en) 1979-12-07 1980-12-08 METHOD FOR PRODUCING 4-BENZYL-ALPHA- (P-HYDROXYPHENYL)-BETA-METHYL-1-PIPERIDINAETHANOL AND ITS SALTS WITH ACIDS.
BR8008020A BR8008020A (en) 1979-12-07 1980-12-08 PROCESS FOR THE PREPARATION OF 1- (4-HYDROXYphenyl) -2- (4-BENZYLPIPERIDINE) -1-PROPANOL AND ITS ACID ADDITION SALTS
AT0597580A AT374181B (en) 1979-12-07 1980-12-09 METHOD FOR PRODUCING 4-BENZYL-ALPHA- (P
HK71984A HK71984A (en) 1979-12-07 1984-09-20 Process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol and acid-addition salts

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP15811279A JPS5681560A (en) 1979-12-07 1979-12-07 Preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1- propanol and its addition salt

Publications (2)

Publication Number Publication Date
JPS5681560A true JPS5681560A (en) 1981-07-03
JPS6239153B2 JPS6239153B2 (en) 1987-08-21

Family

ID=15664557

Family Applications (1)

Application Number Title Priority Date Filing Date
JP15811279A Granted JPS5681560A (en) 1979-12-07 1979-12-07 Preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1- propanol and its addition salt

Country Status (1)

Country Link
JP (1) JPS5681560A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE112006001701T5 (en) 2005-06-27 2008-09-04 Alps Pharmaceutical Ind. Co., Ltd., Hida Process for the preparation of optically active benzylamine derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0655045U (en) * 1993-01-04 1994-07-26 義明 谷西 Ignition device

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS501478U (en) * 1973-05-11 1975-01-09
JPS5059274U (en) * 1973-10-12 1975-06-02

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS501478U (en) * 1973-05-11 1975-01-09
JPS5059274U (en) * 1973-10-12 1975-06-02

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE112006001701T5 (en) 2005-06-27 2008-09-04 Alps Pharmaceutical Ind. Co., Ltd., Hida Process for the preparation of optically active benzylamine derivatives

Also Published As

Publication number Publication date
JPS6239153B2 (en) 1987-08-21

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