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

HRID 254274Notes

Reaction equation

HRID 254274 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

5

Reactant 1

HCID 231207404-[4-(2-Fluorophenyl)piperazin-1-yl]butanenitrile

Product 1

HCID 231207324-(4-(2-Fluorophenyl)piperazin-1-yl)butylamineYield 99%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

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.

Workup

  1. additionthe mixture is introduced in a Parr bottle
  2. filtrationThe catalyst is filtered of
  3. customThe filtrate is evaporated in vacuo
  4. washthe organic layer is washed three times with H2O
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated
  7. additionis added
  8. customThe mixture is evaporated
  9. customthe hydrochloride is crystallized in a mixture of EtOH-Et2O (1-1)

Sources & evidence

ORD record
ord-2435a354b9d64ebb9aed5763a2f06ca0
Source dataset
uspto-grants-2011_01
Patent number
US07875617B2

Reaction notes

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