Hydrochloric Acid → 3-Phenylbutylamine

HRID 897382Notes

Reaction equation

HRID 897382 reaction equation
[C:1]1([CH:7]([CH3:11])[CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:18].[Na+].Cl>CO>[C:1]1([CH:7]([CH3:11])[CH2:8][CH2:9][NH2:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 859793-PhenylbutanalHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 30159623-Phenylbutylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-phenylbutyraldehyde (3 ml, 20.18 mmol), ammonium acetate (15 g, 195 mmol) and sodium cyanoborohydride (900 mg, 14.32 mmol) in methanol (50 ml) was stirred overnight under an argon atmosphere. The reaction was acidified to pH 2 by the addition of conc. HCl. The solvent was evaporated, dichloromethane and water were added, and the aqueous layer was made basic (pH 12) by the addition of solid potassium hydroxide. Extraction (dichloromethane) and concentration gave the title compound as an oil. ES-MS (m/z): 150.2 (M+H)+; 1H NMR (CDCl3): d 7.40-7.17 (m, 5H, Ph), 2.81 (q, 1H, CH), 2.62 (m, 2H, CH2), 1.76 (dq, 2H, CH2), 1.29 (d, 3H, CH3).

Workup

  1. customThe solvent was evaporated
  2. additiondichloromethane and water were added
  3. additionby the addition of solid potassium hydroxide
  4. extractionExtraction (dichloromethane) and concentration

Sources & evidence

ORD record
ord-4e158d7be7784ce4bebc641901e2426e
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

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