2-Chlorobenzyl chloride → Ticlopidine

HRID 568894

Reaction equation

HRID 568894 reaction equation
Cl.[S:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.[Cl:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]Cl.[OH-].[Na+]>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][N:7]1[CH2:8][CH2:9][C:10]2[S:2][CH:3]=[CH:4][C:5]=2[CH2:6]1

Participants

6

Reactant 3

HCID 119062-Chlorobenzyl chlorideHCID 14798Sodium HydroxideHCID 101763424,5,6,7-Tetrahydrothieno(3,2-c)pyridinium chloride

Product 1

HCID 5472TiclopidineYield 80%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 4,5,6,7-tetrahydrothieno-[3,2-c]pyridine hydrochloride (24.0 g, 0.137 mol) and 2-chlorobenzyl chloride (26.4 g, 0.164 mol) in benzene (100 ml) were added an aqueous 2.5N NaOH solution (150 ml, 0.375 mol) and tetra-n-butyl ammonium hydrogen sulfate (1.0 g, 0.003 mol). The mixture was stirred for 40 hours at toom temperature. The reaction mixture was allowed to stand, thereby separating an organic layer from an aqueous layer. The aqueous layer was extracted with benzene (100 ml×2 times). The originally separated organic layer was combined with the extracted benzene layer, and the combined organic layer was washed with water and then with saturated NaCl solution, dried (over K2CO3), and concentrated. The residue was distilled under reduced pressure to prepare 28,8 g (yield 80.0%) of 5-(2-chlorobenzyl)-4,5,6,7tetrahydrothieno[3,2-c]pyridine as an oily product, b.p. 155.0°-158.0° C. (1.5 mmHg).

Workup

  1. customseparating an organic layer from an aqueous layer
  2. extractionThe aqueous layer was extracted with benzene (100 ml×2 times)
  3. washthe combined organic layer was washed with water
  4. dry with materialwith saturated NaCl solution, dried (over K2CO3)
  5. concentrationconcentrated
  6. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-417d9b86c0504b38b5aa0471d1926f9d
Source dataset
uspto-grants-1988_03
Patent number
US04730049

Linked notes

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