Benzenesulfonyl chloride → 1-Benzenesulfonylpiperidine-4-carboxylic Acid [4-(3-dimethylaminopyrrolidin-1-yl)-phenyl]amide

HRID 1354730Notes

Reaction equation

HRID 1354730 reaction equation
[CH3:1][N:2]([CH3:23])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[O:16])=[CH:10][CH:9]=2)[CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[C:30]1([S:36](Cl)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN1CCCC1=O>[CH3:1][N:2]([CH3:23])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]([CH:17]3[CH2:22][CH2:21][N:20]([S:36]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)(=[O:38])=[O:37])[CH2:19][CH2:18]3)=[O:16])=[CH:12][CH:13]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 67147939Piperidine-4-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

Product 1

HCID 588675671-Benzenesulfonylpiperidine-4-carboxylic Acid [4-(3-dimethylaminopyrrolidin-1-yl)-phenyl]amide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Piperidine-4-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide (70 mg) dissolved in N-methylpyrrolidone (2 ml) was mixed with potassium carbonate (45 mg) and benzenesulfonyl chloride (35 mg). After 12 hours, the mixture was filtered and the filtrate was purified by preparative HPLC. This resulted in the product with the molecular weight of 456.61 (C24H32N4O3S); MS (ESI): 457 (M+H+).

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was purified by preparative HPLC
  3. customThis resulted in the product with the molecular weight of 456.61 (C24H32N4O3S)

Sources & evidence

ORD record
ord-a5624133bd374d0aa3ed4064543ab7e9
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

Loading…