t-Butyl 4-(cyanoacetyl)-1-piperazinecarboxylate → Tert-butyl 4-(3-aminopropanoyl)piperazine-1-carboxylate

Reaction equation

[C:1]([CH2:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])#[N:2]>[OH-].[NH4+].CO.[Ni]>[NH2:2][CH2:1][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5]

Participants

Procedure

A mixture of Example 604A (500 mg) was hydrogenated in the presence of Raney® nickel (5 g) in 10 mL of 20% ammonium hydroxide in methanol at room temperature for 16 hours under 60 psi pressure. Insoluble was filtered off and the filtrate was evaporated to dryness and the residue was redissolved in ether. The ethereal solution was passed through membrane filter. The title compound was obtained after ether was removed. 330 mg. MS (ESI(+)) m/e 258 (M+H)−; 1H NMR (300 MHz, DMSO-d6) δ 4.04 (s, 2H), 3.42-3.45 (m, 4H), 3.26-3.33 (m, 42H), 1.41 (s, 9H).