Hydrochloric Acid → HCID 17950730, compound

Reaction equation

[C:1]([CH2:3][CH2:4][CH2:5][NH:6][C:7]1([CH3:17])[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]([CH3:16])([CH3:15])[CH2:8]1)#N.[ClH:18]>C(O)C.[Pd]>[ClH:18].[CH3:17][C:7]1([N:6]2[CH2:5][CH2:4][CH2:3][CH2:1]2)[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]([CH3:16])([CH3:15])[CH2:8]1

Participants

Procedure

N-(3-Cyanopropyl)-1,3,3,5,5-pentamethylcyclohexylamine (2) (1.2 g, 5.1 mmol) in ethanol (120 ml) and conc. HCl (4 ml) was hydrogenated over 10% Pd/C (250 mg) at 7 bar for 40 h (after 24 h additional portion of catalyst (260 mg) was added). The catalyst was removed by filtration through celite pad and solvent evaporated. The residue was treated with acetonitrile, the solids filtered off and the filtrate evaporated. The crude product vas crystallized from ether to give N-(1,3,3,5,5-pentamethylcyclohexyl) pyrrolidine hydrochloride (3) (0.67 g, 49%) with m.p. 156-158° C.