Sulfuric Acid → HCID 68132289, compound

HRID 268293Notes

Reaction equation

HRID 268293 reaction equation
Cl.[Cl:2][C:3]1[CH:23]=[CH:22][C:6]([CH:7](O)[CH2:8][NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)=[CH:5][CH:4]=1.S(=O)(=O)(O)O>O>[ClH:2].[Cl:2][C:3]1[CH:23]=[CH:22][C:6]([CH:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=3)[CH2:10][NH:9][CH2:8]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 68131889HCID 68131889, compound

Product 1

HCID 68132289HCID 68132289, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature with stirring, 7.12 g. of rac.-4-chloro-α-{[(3,4-dimethoxybenzyl)amino]methyl}benzyl alcohol hydrochloride are introduced into 100 ml. of a mixture of equal parts by volume of conc. sulfuric acid and water and heated of 80° for 30 minutes. After rendering alkaline, extraction of the base with methylene chloride, acidification with ethanolic hydrogen chloride and recrystallization from ethanol-ether there is obtained rac.-4-(4-chlorphenyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline hydrochloride of m.p. 186°-187°. The free base displays a m.p. of 118°-119° after recrystallization from ether.

Workup

  1. temperatureheated of 80° for 30 minutes
  2. extractionalkaline, extraction of the base with methylene chloride, acidification
  3. customwith ethanolic hydrogen chloride and recrystallization from ethanol-ether

Sources & evidence

ORD record
ord-0b33d3017d744a3c90250f859377713e
Source dataset
uspto-grants-1976_03
Patent number
US03947456

Reaction notes

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