JPS55111468A - Preparation of n-benzyl-tetrahydro isoquinoline derivative - Google Patents
Preparation of n-benzyl-tetrahydro isoquinoline derivativeInfo
- Publication number
- JPS55111468A JPS55111468A JP1620179A JP1620179A JPS55111468A JP S55111468 A JPS55111468 A JP S55111468A JP 1620179 A JP1620179 A JP 1620179A JP 1620179 A JP1620179 A JP 1620179A JP S55111468 A JPS55111468 A JP S55111468A
- Authority
- JP
- Japan
- Prior art keywords
- benzyl
- derivative
- solvent
- formula
- absence
- 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.)
- Pending
Links
Landscapes
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
PURPOSE: To obtain the title compound which is a raw material for isoquinoline alkaloid in high yield simply through a novel method, by reducing the reaction product of an isochroman-3-one derivative with a p-substituted benzylamine, followed by ring closure.
CONSTITUTION: An isochroman derivative of formula I (R1 is lower alkyl group; R2 is aralkyl group) is reacted with a p-substituted benzylamine in the absence of a solvent, in the presence of preferably N2 gas at 150W200°C for 0.5W2hr, to form a compound of formula II, which is reduced with an agent, e.g. Li(AlH4) in a solvent at room temperature to 100°C, for 1W20hr. The reduction product is subjected to ring closure with a halogenating agent, e.g. thionyl chloride, in the presence or absence of a solvent, under heating or at room temperature to give an N-benzyl-tetrahydroisoquinoline derivative, e.g. o-benzyl-sendaverine, of formula III (R3 is lower alkyl group).
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1620179A JPS55111468A (en) | 1979-02-16 | 1979-02-16 | Preparation of n-benzyl-tetrahydro isoquinoline derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1620179A JPS55111468A (en) | 1979-02-16 | 1979-02-16 | Preparation of n-benzyl-tetrahydro isoquinoline derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS55111468A true JPS55111468A (en) | 1980-08-28 |
Family
ID=11909886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1620179A Pending JPS55111468A (en) | 1979-02-16 | 1979-02-16 | Preparation of n-benzyl-tetrahydro isoquinoline derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55111468A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100863692B1 (en) | 2006-12-08 | 2008-10-15 | 울산대학교 산학협력단 | 7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline derivative with prophylactic effect against degenerative and inflammatory diseases |
| KR100870576B1 (en) * | 2008-08-27 | 2008-11-27 | 울산대학교 산학협력단 | 7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline derivative with prophylactic effect against degenerative and inflammatory diseases |
-
1979
- 1979-02-16 JP JP1620179A patent/JPS55111468A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100863692B1 (en) | 2006-12-08 | 2008-10-15 | 울산대학교 산학협력단 | 7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline derivative with prophylactic effect against degenerative and inflammatory diseases |
| KR100870576B1 (en) * | 2008-08-27 | 2008-11-27 | 울산대학교 산학협력단 | 7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline derivative with prophylactic effect against degenerative and inflammatory diseases |
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