Ammonium Hydroxide → 6-Phenylhexan-1-amine

HRID 1583746Notes

Reaction equation

HRID 1583746 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[N:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[NH4+]>[Ni].C(O)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 104647826-Phenylhexanenitrile

Product 1

HCID 1455586-Phenylhexan-1-amineYield 75.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 42.4 g (0.245 mole) of 6-phenylcapronitrile, 3 g of Raney nickel, 200 ml of ethanol, and 30 ml of concentrated ammonium hydroxide was hydrogenated at 43 psi, and room temperature for 24 hours. The catalyst was removed by filtration and the filtrate concentrated leaving an oil. Distillation under reduced pressure afforded 32.8 g (75.6%) of 6-phenylhexylamine as a colorless oil, bp 118°-123° C./1.5 mm of Hg. NMR (CDCl3): 7.20 (s, 5H); 2.80-2.55 (m, 4H); 1.80-1.10 (m, 8H); 1.00 (s, 2H - exchangeable with D2O).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated
  3. customleaving an oil
  4. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-3d5bde5ee3444c3ca9ffd977f70953f1
Source dataset
uspto-grants-1985_11
Patent number
US04554276

Reaction notes

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