Water → N-(4-phenylcyclohexyl)-N-cyclohexylmethylamine

HRID 37295

Reaction equation

HRID 37295 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:14]1([CH2:20][NH2:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.O>C1C=CC=CC=1>[C:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([NH:21][CH2:20][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 76688CyclohexanemethylamineHCID 786054-Phenylcyclohexanone

Product 1

HCID 19935094N-(4-phenylcyclohexyl)-N-cyclohexylmethylamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 5 g of 4-phenylcyclohexanone and cyclohexylmethylamine in 100 ml of benzene was refluxed for 2 hours with removing water and the solvent was distilled away in vacuo. The residue was dissolved in methanol and to the solution was added 1.5 g of sodium borohydride. The mixture was stirred at room temperature and the solvent was distilled away in vacuo. To the residue was added water and extracted with diethyl ether. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was distilled away to give 7 g of N-(4-phenylcyclohexyl)-N-cyclohexylmethylamine as an oil. (N-(4-phenylcyclohexyl)-N-cyclohexylmethylamine hydrochloride, melting at 267°-270° C. with decomposition)

Workup

  1. distillationthe solvent was distilled away in vacuo
  2. dissolutionThe residue was dissolved in methanol and to the solution
  3. additionwas added 1.5 g of sodium borohydride
  4. distillationthe solvent was distilled away in vacuo
  5. additionTo the residue was added water
  6. extractionextracted with diethyl ether
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-8915cbe5c8664ef18622aa95456bc4f5
Source dataset
uspto-grants-1995_05
Patent number
US05420164

Linked notes

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