Dimethylformamide → N-(1-Phenylprop-1-ene-2-sulfonyl)piperidine-1-carboxamide

HRID 461466Notes

Reaction equation

HRID 461466 reaction equation
[C:1]1([N:7]([C:23]2[CH:28]=CC=CC=2)[C:8]([NH:10][S:11]([C:14]([CH3:22])=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:13])=[O:12])=[O:9])C=CC=[CH:3][CH:2]=1.N1CCCCC1.CN(C)C=O>CCOCC>[N:7]1([C:8]([NH:10][S:11]([C:14]([CH3:22])=[CH:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)(=[O:13])=[O:12])=[O:9])[CH2:1][CH2:2][CH2:3][CH2:28][CH2:23]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8082PiperidineHCID 54322426N-(Diphenylcarbamoyl)-1-phenylprop-1-ene-2-sulfonamide

Product 1

HCID 54049334N-(1-Phenylprop-1-ene-2-sulfonyl)piperidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.9g of N-(N,N-diphenylcarbamoyl)-1-phenylpropene-2-sulfonamide and 1.7g of piperidine in 10ml. of N,N-dimethylformamide is maintained at ca. 95° C. for 6 hours. It is then cooled to ambient temperature, and 100 ml. of ether is added. The mixture is extracted with 50 ml. of water, and then the water extract is acidified using concentrated hydrochloric acid. This causes the crude product to precipitate. It is filtered off, and then it is recrystallized from a mixture of acetone and water giving 670 mg. of N-(piperidinocarbonyl)-1-phenylpropene-2-sulfonamide, m.p. 159°-161° C.

Workup

  1. extractionThe mixture is extracted with 50 ml
  2. extractionof water, and then the water extract
  3. customto precipitate
  4. filtrationIt is filtered off
  5. customit is recrystallized from a mixture of acetone and water giving 670 mg

Sources & evidence

ORD record
ord-1ed06eaeb7b749698a4d5dc2f2483c5c
Source dataset
uspto-grants-1977_12
Patent number
US04062960

Reaction notes

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