Potassium Carbonate → HCID 13556648, compound

HRID 280047Notes

Reaction equation

HRID 280047 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][S:12]([CH2:15][CH2:16][CH2:17]Cl)(=[O:14])=[O:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:25][NH:26][CH2:27][CH2:28][C:29]1[CH:38]=[CH:37][C:34]([O:35][CH3:36])=[C:31]([O:32][CH3:33])[CH:30]=1>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][S:12]([CH2:15][CH2:16][CH2:17][N:26]([CH2:27][CH2:28][C:29]2[CH:38]=[CH:37][C:34]([O:35][CH3:36])=[C:31]([O:32][CH3:33])[CH:30]=2)[CH3:25])(=[O:14])=[O:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77039N-MethylhomoveratrylamineHCID 13556647HCID 13556647, compound

Product 1

HCID 13556648HCID 13556648, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

N-(3,5-Dimethoxyphenyl)-3-chloro-1-propanesulfonamide prepared in the preceding paragraph (16.56 g, 0.057 mol) was dissolved in xylene (300 mL) containing potassium carbonate (7.86 g, 0.057 mol) and N-methylhomoveratrylamine (11.13 g, 0.057 mol) and the reaction warmed and stirred three days. Filtration, stripping of solvent and chromatography on dry-column silica gel (1100 g) with 5% methanol/ethyl acetate provided crude N-(3,5-dimethoxyphenyl)-3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]-1-propanesulfonamide (5.32 g).

Workup

  1. temperaturethe reaction warmed
  2. filtrationFiltration

Sources & evidence

ORD record
ord-afba06cc02714badb32f3752c3cfe883
Source dataset
uspto-grants-1986_05
Patent number
US04587360

Reaction notes

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