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4-Toluenesulfonyl chloride → toluene-4-sulfonic acid 1-(3-chloro-4-fluorobenzoyl)-4-fluoropiperidin-4-yl-methyl Ester

HRID 376303
ノート
印刷プレビュー

反応式

HRID 376303 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[F:12][C:13]1([CH2:29][OH:30])[CH2:18][CH2:17][N:16]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([Cl:28])[CH:22]=2)=[O:20])[CH2:15][CH2:14]1>N1C=CC=CC=1>[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[F:27])[C:19]([N:16]1[CH2:17][CH2:18][C:13]([CH2:29][O:30][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])([F:12])[CH2:14][CH2:15]1)=[O:20]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 10755891(3-Chloro-4-fluorophenyl)[4-fluoro-4-(hydroxymethyl)-1-piperidinyl]methanone

生成物 1

HCID 10718129toluene-4-sulfonic acid 1-(3-chloro-4-fluorobenzoyl)-4-fluoropiperidin-4-yl-methyl Ester収率 76%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

4.87 g of para-toluenesulfonyl chloride (25.5 mmol) are slowly added to a solution of 6.70 g of (4-fluoro-4-hydroxymethylpiperidin-1-yl)-(3-chloro-4-fluorophenyl)methanone (23.12 mmol) in 40 ml of pyridine cooled to 0° C. and maintained under a nitrogen atmosphere. The mixture is stirred for 12 hours at room temperature and then it is poured into ice-cold water, extracted with chloroform and then the organic phase is washed with a 1N aqueous solution of hydrochloric acid. The organic phase is dried over magnesium sulfate, filtered and then concentrated under vacuum. The title product is purified by recrystallization from a dichloromethane/diisopropyl ether mixture. 7.73 g of a white crystalline powder are obtained.

後処理

  1. temperaturemaintained under a nitrogen atmosphere
  2. additionit is poured into ice-cold water
  3. extractionextracted with chloroform
  4. washthe organic phase is washed with a 1N aqueous solution of hydrochloric acid
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe title product is purified by recrystallization from a dichloromethane/diisopropyl ether mixture

出典と根拠

ORDレコード
ord-6e396fbc82ea49309e020cb61aff24ea
出典データセット
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06020345

反応ノート

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