Hydrochloric Acid → Ticlopidine

HRID 358816

反応式

HRID 358816 の反応式
[H-].[Na+].[S:3]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[CH:5]=[CH:4]1.[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Cl.Cl>C1COCC1.C1(C)C=CC=CC=1>[CH:18]1[CH:19]=[CH:20][C:13]([Cl:12])=[C:14]([CH2:15][N:8]2[CH2:7][C:6]3[CH:5]=[CH:4][S:3][C:11]=3[CH2:10][CH2:9]2)[CH:17]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 119062-Chlorobenzyl chlorideHCID 24758Sodium hydrideHCID 30850764,5,6,7-Tetrahydrothieno(3,2-c)pyridine

生成物 1

HCID 5472Ticlopidine

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of sodium hydride (0.42 g, 8.6 mmole) in THF (5.0 ml) is added a solution of 4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (1.0 g, 7.2 mmole), prepared, for example, as described in Example A-2, in THF (10 ml). The mixture is stirred under a nitrogen atmosphere at room temperature for 30 minutes and o-chlorobenzyl chloride (1.74 g, 10.8 mmole) is added. After stirring at room temperature for 90 minutes, toluene (15 ml) is added and the mixture is heated to reflux for 15 to 20 hours. Disappearance of starting material is confirmed by TLC. The mixture is then cooled to room temperature and acidified with 40 ml 1N hydrochloric acid. The organic layer is separated. The aqueous layer is extracted with 50 ml of toluene. The aqueous layer is then separated and basified with dilute aqueous sodium hydroxide to pH 13-14. The product is extracted into methylene chloride (3×40 ml). The methylene chloride extracts are washed (1×50 ml water) and 1×50 ml salt solution) then dried over anhydrous magnesium sulfate and concentrated to give the desired product.

後処理

  1. stirringAfter stirring at room temperature for 90 minutes
  2. temperaturethe mixture is heated
  3. temperatureto reflux for 15 to 20 hours
  4. temperatureThe mixture is then cooled to room temperature
  5. customThe organic layer is separated
  6. extractionThe aqueous layer is extracted with 50 ml of toluene
  7. customThe aqueous layer is then separated
  8. extractionThe product is extracted into methylene chloride (3×40 ml)
  9. washThe methylene chloride extracts are washed (1×50 ml water) and 1×50 ml salt solution)
  10. dry with materialthen dried over anhydrous magnesium sulfate
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-3ba873efaad442deaf4217595a99d2ea
出典データセット
uspto-grants-1991_03
特許番号
US04997945

関連ノート

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