반응 #48062

반응 방정식

2-chloro-4-ethynyl-pyridine

4-tert-butyl-benzylamine

acetic acid

sodium cyanoborohydride

→

title compound

수율 55.4%

(4-tert-butyl-benzyl)-[2-(2-chloro-pyridin-4-yl)-ethyl]-amine

수율 55.4%

용매

NaOH

ethanol

반응 조건

후처리

1. 1
   온도to cool to RT
2. 2
   추출extracted with DCM
3. 3
   세척The combined organic extracts were washed with saturated NaHCO3 solution and brine
4. 4
   건조dried (Na2SO4)
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo

실험 절차

A mixture of 1.386 g of 2-chloro-4-ethynyl-pyridine (10.07 mmol), 2.65 ml of 4-tert-butyl-benzylamine (15.11 mmol), 0.58 ml of acetic acid (10.07 mmol) and 666 mg of sodium cyanoborohydride (95% purity, 10.07 mmol) in ethanol (12 ml) were heated to 105° C. in a sealed tube for 2 d. The reaction mixture was allowed to cool to RT, diluted with 3N NaOH solution and extracted with DCM. The combined organic extracts were washed with saturated NaHCO3 solution and brine, dried (Na2SO4), filtered and concentrated in vacuo. After column chromatography (heptane/EtOAc 100:0 to 0:100) 1.688 g (55%) of the title compound were isolated as a brown liquid. MS (ISP) 303.2 (M+H)+.

출처