Ammonia → Benzylamine

HRID 1624918Notes

Reaction equation

HRID 1624918 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-a89bfa1febf9446e83c2610de761b646
Source dataset
uspto-grants-2014_07
Patent number
US08779136B2

Reaction notes

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