2-Chlorobenzyl chloride → Ticlopidine

HRID 568893

反応式

HRID 568893 の反応式
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+].[OH-].C[N+](C)(C)CC1C=CC=CC=1>C1C=CC=CC=1>[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

参加物

6

反応物 4

HCID 119062-Chlorobenzyl chlorideHCID 14798Sodium HydroxideHCID 66854Benzyltrimethylammonium hydroxideHCID 101763424,5,6,7-Tetrahydrothieno(3,2-c)pyridinium chloride

生成物 1

HCID 5472Ticlopidine収率 74.7%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To a solution of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (580 mg, 3.3 mmol) and 2-chlorobenzyl chloride (640 mg, 3.9 mmol) in benzene (5.0 ml) were added an aqueous 5M NaOH solution (5 ml), and trimethylbenzyl ammonium hydroxide (100 mg of 40% methanol solution). The mixture was stirred for 40 hours at room temperature. The reaction mixture was allowed to stand, thereby separating an aqueous layer from an organic layer The organic layer was washed with water and then with saturated NaCl solution, dried (over MgSO4) and concentrated. The residue was purified by silica gel column chromatography to prepare 650 mg (yield 74.7%) of 5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine as an oily product, b.p. 155.0°-158.0° C. (1.5 mmHg). This pyridine was dissolved in hydrogen chloride saturated ethyl alcohol (5 ml) and the solution was then concentrated and cooled. The precipitated hydrochloride was filtered off and dried. The yield 420 mg (42.4%), m.p. 190° C.

後処理

  1. customseparating an aqueous layer from an organic layer The organic layer
  2. washwas washed with water
  3. dry with materialwith saturated NaCl solution, dried (over MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-26befbbe4f9045f9a7ec0d1d4d99ce9a
出典データセット
uspto-grants-1988_03
特許番号
US04730049

関連ノート

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