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

HRID 634835노트

반응식

HRID 634835 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-673d16999b4a4c59965c5581913d1853
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06184242B2

반응 노트

불러오는 중…