Benzenamine, 4-(phenylmethyl)- → Cyclohexanamine, 4-(cyclohexylmethyl)-

HRID 1576493Notes

Reaction equation

HRID 1576493 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.C[O-].[K+].[H][H]>[Ru]>[CH2:1]1[CH2:2][CH2:3][CH:4]([CH2:7][CH:8]2[CH2:9][CH2:10][CH:11]([NH2:14])[CH2:12][CH2:13]2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 136914Benzenamine, 4-(phenylmethyl)-HCID 23664618Potassium methoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 299588Cyclohexanamine, 4-(cyclohexylmethyl)-

Reagents, catalysts & solvents 1

HCID 23950RutheniumCatalyst

Conditions

Temperature
290 °C

Procedure

In a steel autoclave fitted with a stirring apparatus and a product draw off system retaining the catalyst in the reactor can be placed 200 parts of 4-aminodiphenylmethane as described in British Patent 764,633 and 100 parts of a finely divided 5% ruthenium on an alumina support and 15 parts of potassium methoxide. The mixture within the autoclave can then be heated to 290°C with stirring and hydrogen added to maintain a pressure of 290 atmospheres for 20 minutes. The resulting mixture can then be freed of catalyst by filtration and distilled to strip off solvent. Final distillation under vacuum can then be used to provide the desired product, 4-aminodicyclohexylmethane, which is a colorless viscose liquid.

Workup

  1. temperatureto maintain a pressure of 290 atmospheres for 20 minutes
  2. filtrationThe resulting mixture can then be freed of catalyst by filtration
  3. distillationdistilled
  4. distillationFinal distillation under vacuum

Sources & evidence

ORD record
ord-3d9046b793864de19c3a8d98b547d81f
Source dataset
uspto-grants-1976_09
Patent number
US03981766

Reaction notes

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