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

HRID 337200Notes

Reaction equation

HRID 337200 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-f68cd96e3f7d4231a1d59bb8d49a3765
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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