4-[4-(2-Fluorophenyl)piperazin-1-yl]butanenitrile → 4-(4-(2-Fluorophenyl)piperazin-1-yl)butylamine

Reaction equation

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

Participants

Procedure

1-(3-Cyanopropyl)-4-(2-fluoro phenyl)piperazine (2 g) was dissolved in a mixture of methanol and aqueous ammonia 28% (1-1, 20 ml) and the mixture is introduced in a Parr bottle. Then, Raney nickel (500 mg) is added as catalyst, and the mixture is hydrogenated in a Parr apparatus for 12 h under 60 psi. The catalyst is filtered of. The filtrate is evaporated in vacuo and the residue is taken of with AcOEt, the organic layer is washed three times with H2O, dried over anhydrous Na2SO4 and evaporated. The residue is taken with EtOH and concentrated HCl (15 mL 37%) is added. The mixture is evaporated and the hydrochloride is crystallized in a mixture of EtOH-Et2O (1-1) to yield the title compound B3 (99%). 1H NMR (200 MHz, CDCl3) δ: 1.44-1.61 (m, 4H), 1.88 (s, 2H), 2.37-2.45 (t, 2H), 2.60-2.65 (t, 4H), 2.65-2.72 (t, 2 H), 3.09-3.14 (t, 4H), 6.90-7.08 (m, 4H). RMN 13C (50 MHz, CDCl3): δ 24.2, 31.6, 42.0, 50.4, 53.2, 58.4, 115.7, 118.8, 122.3, 124.4, 142.8, 158.1.