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

HRID 337200ノート

反応式

HRID 337200 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-f68cd96e3f7d4231a1d59bb8d49a3765
出典データセット
uspto-grants-2014_11
特許番号
US08889716B2

反応ノート

読み込み中…