Acetone → 2-(Hexahydro-1H-azepin-1-yl)-2-methylpropanenitrile

HRID 20820Notes

Reaction equation

HRID 20820 reaction equation
Cl.[NH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CC(C)=O.[C-]#N.[K+].CN(C)[C:18]1([C:23]#[N:24])[CH2:22]CC[CH2:19]1>O>[N:2]1([C:18]([CH3:22])([CH3:19])[C:23]#[N:24])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 9032Potassium CyanideHCID 107730491-(Dimethylamino)cyclopentanecarbonitrileHCID 119716651H-Azepine, hexahydro-, hydrochloride

Product 1

HCID 164482452-(Hexahydro-1H-azepin-1-yl)-2-methylpropanenitrileYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound (6.6 g: 80%) was prepared from homopiperidine hydrochloride (6.7 g; 49 mmol), acetone (3.67 ml; 50 mmol), and potassium cyanide (3.25 g; 50 mmol) in water (25 ml) in a similar manner to that described in D1. 1H NMR (CDCl3) δ 1.43 (6H, s), 1.50-1.65 (8H, m), 2.66 (4H, m).

Sources & evidence

ORD record
ord-e013f3b38f9149ffa440cbfd1fb00ef4
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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