Benzenesulfonyl chloride → 2,2,2-trifluoro-N-(4-(1-benzenesulfonyl-piperidin-4-ylmethyl)-phenyl]acetamide

HRID 634835ノート

反応式

HRID 634835 の反応式
[F:1][C:2]([F:20])([F:19])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:8][CH:7]=1)=[O:4].C(N(CC)CC)C.[C:28]1([S:34](Cl)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[F:20][C:2]([F:1])([F:19])[C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH:13]2[CH2:14][CH2:15][N:16]([S:34]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:36])=[O:35])[CH2:17][CH2:18]2)=[CH:10][CH:11]=1)=[O:4]

参加物

5

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 218767392,2,2-trifluoro-N-(4-(piperidin-4-ylmethyl)-phenyl]acetamide

生成物 1

HCID 218770242,2,2-trifluoro-N-(4-(1-benzenesulfonyl-piperidin-4-ylmethyl)-phenyl]acetamide収率 57%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 2,2,2-trifluoro-N-[4-(piperidin-4-ylmethyl)-phenyl]acetamide (0.5 g, 1.75 mmol) and triethylamine (0.23 g, 2.1 mmol) in dichloromethane (10 mL) was cooled in an ice bath under nitrogen atmosphere. A solution of benzenesulfonyl chloride (0.37 9, 2.1 mmoL) in dichloromethane (1 mL) was added under to the mixture while stirring. After 2 hours, the reaction mixture was quenched with water. The separated organic layer was washed with cold water and brine, dried, and solvents removed in vacuo. The residue was crystallized from ethyl acetate/hexanes to give 2,2,2-trifluoro-N-[4-(1-benzenesulfonyl-piperidin-4-ylmethyl)-phenyl]acetamide (0.43 g, 57%), m.p. 194-195° C.; Analysis for C20H21N2O3SF3: Calc.: C, 56.32; H, 4.96; N, 6.57; Found: C, 56.54; H, 4.99; N, 6.68.

後処理

  1. temperaturewas cooled in an ice bath under nitrogen atmosphere
  2. customthe reaction mixture was quenched with water
  3. washThe separated organic layer was washed with cold water and brine
  4. customdried
  5. customsolvents removed in vacuo
  6. customThe residue was crystallized from ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-673d16999b4a4c59965c5581913d1853
出典データセット
uspto-grants-2001_02
特許番号
US06184242B2

反応ノート

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