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

HRID 2426676
Notes
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Reaction equation

HRID 2426676 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 13387
N-methyl-2-pyrrolidone
Solvent

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-70be513eb78b4bf2b1483b16cd5ce435
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07968550B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes