Reaktion #1150803

Reaktionsgleichung

4-(trifluoromethyl)-benzenesulfonyl chloride

trans-4-methylamino-cyclohexanol

N,N-diisopropylethylamine

→

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

Ausbeute 77.0%

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe organic phase was extracted with 1M KHSO4
2. 2
   WaschenThe combined organic phases were washed with brine
3. 3
   Trocknendried over Na2SO4
4. 4
   Sonstigeevaporated

Vorschrift

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

Quelle