Acetone → 2-(3-Azabicyclo[3.1.0]hex-3-yl)-2-methylpropanenitrile

HRID 20796Notes

Reaction equation

HRID 20796 reaction equation
Cl.[CH:2]12[CH2:7][CH:6]1[CH2:5][NH:4][CH2:3]2.CC(C)=O.[C-]#N.[K+].CN(C)[C:17]1([C:22]#[N:23])[CH2:21]CC[CH2:18]1>O>[CH:2]12[CH2:7][CH:6]1[CH2:5][N:4]([C:17]([CH3:21])([CH3:18])[C:22]#[N:23])[CH2:3]2

Participants

6

Reactant 4

HCID 180AcetoneHCID 9032Potassium CyanideHCID 107730491-(Dimethylamino)cyclopentanecarbonitrileHCID 223352893-Azabicyclo[3.1.0]hexane hydrochloride

Product 1

HCID 593478472-(3-Azabicyclo[3.1.0]hex-3-yl)-2-methylpropanenitrileYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound (583 mg, 84%) was prepared from 3-azabicyclo[3.1.0]hexane hydrochloride (550 mg, 4.6 mmol) [Pestic. Chem: Hum. Welfar Environ., Proc, Int, Congr. Pestic. Che., 5th, 1982, 1,159-64, 1983], acetone (267 mg, 4.6 mmol) and potassium cyanide (300 mg, 4.6 mmol) in water (2.5 ml) in a similar manner to that described in D1. 1H NMR (CDCl3) δ: 0.40 (1H, m), 0.58 (1H, m), 1.43 (8H, m), 2.64 (2H, m), 3.10 (2H, d, J=8 Hz).

Sources & evidence

ORD record
ord-c1d6d633b3744333897c64fb2c8e38db
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

Loading…