Sodium hydride → N-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-N-(1-methylethyl)-3-(trifluoromethyl)benzenesulfonamide

HRID 1719435Notes

Reaction equation

HRID 1719435 reaction equation
[CH:1]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:21][CH2:22][CH2:23][N:24]([CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1)[CH3:25]>CN(C)C=O>[CH3:37][O:36][C:30]1[CH:29]=[C:28]([CH2:27][CH2:26][N:24]([CH3:25])[CH2:23][CH2:22][CH2:21][N:4]([CH:1]([CH3:3])[CH3:2])[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)(=[O:7])=[O:6])[CH:33]=[CH:32][C:31]=1[O:34][CH3:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 577693N-(3-Chloropropyl)-3,4-dimethoxy-N-methylphenethylamineHCID 23323137N-isopropyl-3-trifluoromethylbenzenesulfonamide

Product 1

HCID 54053041N-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-N-(1-methylethyl)-3-(trifluoromethyl)benzenesulfonamideYield 43.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-isopropyl-3-trifluoromethylbenzenesulfonamide (5.362 g, 0.02 mol) in dimethylformamide (30 mL) was treated with sodium hydride (60% in mineral oil), (0.802 g) and stirred for 2 hours. Then N-(3-chloropropyl)-3,4-dimethoxy-N-methylphenethylamine (5.436 g, 0.02 mol) was added and the reaction heated overnight. Filtration and removal of solvent provided the crude product (6.95 g). Column chromatography and high pressure liquid chromatography provided the pure product (4.35 g) as a gum. 1H NMR (CDCl3) 1.15 (d, 6, J=3.5H, Me2) 2.25 (s, 3, N--Me) 3.84 (d, 6, (OMe)2) 6.76 (m, 3, Ar) 7.25 (m, 3, Ar).

Workup

  1. temperaturethe reaction heated overnight
  2. filtrationFiltration and removal of solvent
  3. customprovided the crude product (6.95 g)

Sources & evidence

ORD record
ord-3bb134aecc594bbb99d7ed48eaac7667
Source dataset
uspto-grants-1985_09
Patent number
US04539426

Reaction notes

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