Réaction #53825

Équation de réaction

4-(trifluoromethyl)-benzenesulfonyl chloride

trans-4-Methylamino-cyclohexanol

N,N-diisopropylethylamine

→

trans-N-(4-Hydroxy-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide

Rendement 77.0%

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Extractionthe organic phase extracted with 1M KHSO4
2. 2
   LavageThe combined organic phases were washed with brine
3. 3
   Séchagedried over Na2SO4
4. 4
   Autreevaporated

Mode opératoire

To 3 g (23.2 mmol) trans-4-Methylamino-cyclohexanol in 120 ml CH2Cl2 were added 4.2 ml (24.4 mmol, 1.05 eq) N,N-diisopropylethylamine followed by 5.96 g (24.4 mmol, 1.05 eq) 4-(trifluoromethyl)-benzenesulfonyl chloride in 50 ml CH2Cl2. The mixture was stirred at RT over night and the organic phase extracted with 1M KHSO4, followed by 5% NaHCO3 and brine. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated. Column chromatography on silica gel with hexane:EtOAc 1:1 yielded 6.0 g (77%) trans-N-(4-Hydroxy-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide as off-white solid, MS: 338 (MH+).

Source