Benzylamine → Benzenemethanamine, N-cyclohexyl-

HRID 325754Notes

Reaction equation

HRID 325754 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.P(O)(O)O>C1C=CC=CC=1.O>[CH2:8]([NH:15][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 7967CyclohexanoneHCID 107909Phosphorous acid

Product 1

HCID 204463Benzenemethanamine, N-cyclohexyl-

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

The imine from cyclohexanone and benzylamine was prepared in benzene in the normal way. To this imine (37.4 g; 0.2 mole) was added phosphorous acid (16.4 g; 0.2 mole) and the mixture stirred while heating. The reaction mixture became a homogeneous liquid at 70° and at 95°-100° a vigorous reaction took place. After keeping at 110°-130° for 30 minutes the mixture was cooled and diluted with water. Basification with NaOH and extraction with benzene gave after evaporation of the solvent N-benzylcyclohexylamine (80%). Distillation gave pure N-benzylcyclohexylamine bp 120°-125°/3 mm.

Workup

  1. temperaturewhile heating
  2. customat 70°
  3. customat 95°-100° a vigorous reaction
  4. temperaturethe mixture was cooled
  5. extractionBasification with NaOH and extraction with benzene
  6. customgave
  7. customafter evaporation of the solvent N-benzylcyclohexylamine (80%)
  8. distillationDistillation

Sources & evidence

ORD record
ord-56123171bea34f7e97c9dab7b7c22cb5
Source dataset
uspto-grants-1984_04
Patent number
US04442286

Reaction notes

Loading…