Ammonia → Benzylamine

HRID 2043801Notes

Reaction equation

HRID 2043801 reaction equation
[NH3:1].[CH2:2]([OH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1(C)C=CC=CC=1>[CH2:2]([NH2:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:2](=[N:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:2]([OH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 222Ammonia2×HCID 244Benzyl Alcohol

Product 3

HCID 244Benzyl AlcoholHCID 7504BenzylamineYield 64.6%HCID 95831Benzenemethanamine, N-(phenylmethylene)-Yield 19.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To test whether increasing the concentration of ammonia relative to the alcohol might reduce the formation of imines (for example by capturing the contemplated intermediate aldehyde and preventing its reaction with the primary amine), complex 1 (0.01 mmol), benzyl alcohol (2.5 mmol) and ammonia (8 atm) in toluene were heated under reflux in a Fischer-Porter tube for 130 min, to get benzylamine (64.6%) and N-benzylidenebenzylamine (19.3%) whereas the conversion of benzyl alcohol was 84.7% (compare to entry 6, Table 1). Thus, increasing the concentration of ammonia did not affect the extent of formation of imine.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux in a Fischer-Porter tube for 130 min

Sources & evidence

ORD record
ord-c1aec8f4ec984aafb6ca6a0a3efef748
Source dataset
uspto-grants-2013_11
Patent number
US08586742B2

Reaction notes

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