Acryloyl chloride → N-[1-(4-Nitro-benzenesulfonyl)-piperidin-4-yl]-acrylamide

HRID 337200노트

반응식

HRID 337200 반응식
C(N(C(C)C)CC)(C)C.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:22]2[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1)([O-:12])=[O:11].[C:29](Cl)(=[O:32])[CH:30]=[CH2:31]>C(Cl)Cl>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([S:19]([N:22]2[CH2:23][CH2:24][CH:25]([NH:28][C:29](=[O:32])[CH:30]=[CH2:31])[CH2:26][CH2:27]2)(=[O:20])=[O:21])=[CH:17][CH:18]=1)([O-:12])=[O:11]

참가 물질

5

반응물 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 284183251-(4-Nitrobenzenesulfonyl)piperidin-4-amine

생성물 1

HCID 71618272N-[1-(4-Nitro-benzenesulfonyl)-piperidin-4-yl]-acrylamide수율 99.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diisopropylethylamine (6.8 ml, 41.5 mmol) was added in one portion to a stirred solution of 1-(4-nitro-benzenesulfonyl)-piperidin-4-ylamine (2.36 g, 8.3 mmol) in DCM (10 ml) followed by the drop wise addition of acryloyl chloride (0.78 ml, 9.1 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the resulting precipitate was collected by filtration, washed with water and dried under vacuum to give the title compound (2.80 g, 98% yield) as a white solid. δH (500 MHz, DMSO) 8.39-8.51 (m, 2 H) 7.95-8.10 (m, 3 H) 6.11-6.21 (m, 1 H) 6.01-6.10 (m, 1 H) 5.56 (dd, J=10.09, 2.20 Hz, 1 H) 3.61-3.68 (m, 1 H) 3.52-3.60 (m, 2 H) 2.56-2.66 (m, 2 H) 1.83 (dd, J=13.20, 3.30 Hz, 2 H) 1.36-1.47 (m, 2 H). Tr=1.63 min, m/z (ES+) (M+H)+ 340.

후처리

  1. filtrationAfter this time the resulting precipitate was collected by filtration
  2. washwashed with water
  3. customdried under vacuum

출처 및 근거

ORD 기록
ord-f68cd96e3f7d4231a1d59bb8d49a3765
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889716B2

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