Hexahydro-1H-azepine-1-acetonitrile → Hexahydro-1H-azepine-1-ethanamine

HRID 1669206

Reaction equation

HRID 1669206 reaction equation
[CH2:1]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]#[N:10])[CH2:4][CH2:3][CH2:2]1>[Ni].CCO>[N:5]1([CH2:8][CH2:9][NH2:10])[CH2:6][CH2:7][CH2:1][CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 1

HCID 41164Hexahydro-1H-azepine-1-acetonitrile

Product 1

HCID 40002Hexahydro-1H-azepine-1-ethanamineYield 35.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of nitrile 290 (5.58 g, 40.4 mmol) and Raney Nickel (50% w/w in water, ca. 5 mL) in EtOH (50 mL) and cNH3 (4 mL) was stirred under H2 (60 psi) for 16 h. The mixture was filtered through Celite, washed with EtOH (3×10 mL) and the solvent evaporated to give crude diamine 291 as an oil (2.03 g, 35%) which was used without further purification: 1H NMR δ 2.72 (t, J=6.1 Hz, 2H, CH2N), 2.60-2.68 (m, 4H, 2×CH2N), 2.53 (t, J=6.1 Hz, 2H, CH2N), 1.55-1.66 (m, 10H, 4×CH2, NH2).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with EtOH (3×10 mL)
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-ff3b8ebcc95e4f218406e6e70ae91b26
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Linked notes

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