2-Chlorobenzyl chloride → Ticlopidine

HRID 568894

반응식

HRID 568894 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 5472Ticlopidine수율 80%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 241Benzene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-417d9b86c0504b38b5aa0471d1926f9d
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04730049

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