Potassium Carbonate → 1-(Butane-1-sulfonyl)piperidine-4-carboxylic Acid [4-(3-dimethylaminopyrrolidin-1-yl)-phenyl]amide

HRID 1354732Notes

Reaction equation

HRID 1354732 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+].[CH2:30]([S:34](Cl)(=[O:36])=[O:35])[CH2:31][CH2:32][CH3:33]>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:34]([CH2:30][CH2:31][CH2:32][CH3:33])(=[O:36])=[O:35])[CH2:19][CH2:18]3)=[O:16])=[CH:12][CH:13]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754301-Butanesulfonyl chlorideHCID 67147939Piperidine-4-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

Product 1

HCID 588668061-(Butane-1-sulfonyl)piperidine-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 butylsulfonyl chloride (30 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 436.62 (C22H36N4O3S); MS (ESI): 437 (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 436.62 (C22H36N4O3S)

Sources & evidence

ORD record
ord-9c132d16f69647fb8c8c64891aeeaf18
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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