반응 #49125

반응 방정식

HCl

(±)-2-chloro-N-[[1-(methylamino)cyclopentyl](phenyl)methyl]-3-(trifluoromethyl)benzamide

cyclopropanecarboxaldehyde

sodium triacetoxyborohydride

→

title product

(±)-2-Chloro-N-[{1-[(cyclopropylmethyl)(methyl)amino]cyclopentyl}(phenyl)methyl]-3-(trifluoromethyl)benzamide hydrochloride

용매

DCM

ether

1,2-dichloroethane

반응 조건

후처리

1. 1
   세척washed with saturated potassium carbonate solution and brine
2. 2
   건조dried (Na2SO4)
3. 3
   기타evaporated in vacuo
4. 4
   기타The mixture was separated by column chromatography on silica gel using 20% ether in n-pentane to 2% methanol in ether
5. 5
   기타The oil obtained

실험 절차

To a solution (±)-2-chloro-N-[[1-(methylamino)cyclopentyl](phenyl)methyl]-3-(trifluoromethyl)benzamide E22 (143 g; 0.35 mmol), cyclopropanecarboxaldehyde (0.026 ml; 0.035 mmol) and acetic acid (3 drops) in 1,2-dichloroethane (10 ml) was added sodium triacetoxyborohydride (303 mg; 1.4 mmol). The resulting mixture was allowed to stir at room temperature under argon overnight. Then the reaction mixture was diluted with DCM (20 ml), washed with saturated potassium carbonate solution and brine, dried (Na2SO4) and evaporated in vacuo. The mixture was separated by column chromatography on silica gel using 20% ether in n-pentane to 2% methanol in ether. The oil obtained was treated with 1M HCl in ether to give the title product as an off white hydrochloride salt (0.054 g; 33%). Mass Spectrum (Electrospray LC/MS). Found 465 (MH+). C25H2835ClF3N2O requires 464. Ret. time: 2.30 min.

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