반응 #685018

반응 방정식

sodium cyanide

ammonium hydroxide

1-(benzyloxycarbonyl)-4-piperidinone

ammonium chloride

HCl

→

title compound

수율 100.0%

Benzyl 4-amino-4-cyanopiperidine-1-carboxylate

수율 100.0%

용매

methanol

반응 조건

후처리

1. 1
   추출The mixture was extracted with CH2Cl2 two times
2. 2
   건조dried (Na2SO4)
3. 3
   농축concentrated
4. 4
   workup.DISSOLUTIONThe pale yellow oil was dissolved in CH2Cl2
5. 5
   workup.STIRRINGThe resulting white suspension was stirred at room temp 18 h
6. 6
   여과The solid was collected by filtration

실험 절차

To a stirred mixture of ammonium hydroxide (856 mL), 1-(benzyloxycarbonyl)-4-piperidinone (1.07 mol) and ammonium chloride (113.42 g, 2.14 mol) in methanol (350 mL) was added sodium cyanide (105 g, 2.14 mmol) and stirred at room temperature for 36 h. The mixture was extracted with CH2Cl2 two times. The organic phases were combined and dried (Na2SO4) and concentrated. The pale yellow oil was dissolved in CH2Cl2 and ethereal HCl was added (699 mL, 1.4 mol, 2 M solution). The resulting white suspension was stirred at room temp 18 h. The solid was collected by filtration to give the title compound as white solid (314.5 g, 100% yield). 1H NMR (300 MHz, CDCl3) δ: 7.33-7.27 (5H, m), 5.10 (2H, s), 4.00-3.97 (2H, m), 3.25 (2H, td, J=12.2, 2.8 Hz), 1.97-1.93 (2H, m), 1.78 (2H, s), 1.65-1.59 (2H, m).

출처