Reaction #49100

Reaction equation

D1

1-(dimethylamino)cyclopentanecarbonitrile

phenyl lithium

sodium borohydride

D2

Racemic {1-[amino(phenyl)methyl]cyclopentyl}dimethylamine

1-(dimethylamino)cyclohexanecarbonitrile

dimethylamine hydrochloride

cyclohexanone

potassium cyanide

→

title compound

Yield 36.0%

(±){1-[Amino(phenyl)methyl]cyclohexyl}dimethylamine

Yield 36.0%

Solvents

dibutyl ether

THF

water

Conditions

Procedure

The title compound was prepared in two stages from (i) dimethylamine hydrochloride (3.26 g, 0.04 mol), cyclohexanone (3.9 g, 0.04 mol) and potassium cyanide (2.60 g, 0.04 mol) in water (25 ml) in a similar manner to that described in D1 to make 1-(dimethylamino)cyclohexanecarbonitrile (6.6 g, 100%). This was reacted directly in (ii) with phenyl lithium in dibutyl ether (10.5 ml of a 1.9M solution, 0.02 mol) in THF (30 ml) followed by sodium borohydride (1.51 g, 0.04 mol) in a similar manner to that described in D2 to afford the title compound (2.5 g, 36%). 1H NMR (CDCl3) δ: 0.85 (1H, m), 1.00 (1H, m), 1.25 (2H, m), 1.35-1.60 (6H, br m), 1.70 (1H, m), 2.10 (1H, m), 2.46 (6H, s), 4.15 (1H, s), 7.20-7.32 (5H, m).

Source