Methylamine → HCID 178484783, compound

HRID 1699407Notes

Reaction equation

HRID 1699407 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.[CH3:14][NH2:15]>C1(C)C=CC=CC=1>[CH3:14][NH:15][C@H:10]1[CH2:11][CH2:12][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 786054-Phenylcyclohexanone

Product 1

HCID 178484783HCID 178484783, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

26 g (0.15 mol) of 4-phenylcyclohexanone are stirred with 160 ml of a 6 % methylamine solution in toluene in the presence of 30 g of molecular sieve M 3 Å overnight in a sealed flask. After filtering and concentration by evaporation the residue is dissolved in 200 ml of methanol and at −20° C. 7.8 g sodium borohydride are added batchwise. After it has all been added the mixture is stirred overnight at ambient temperature. After evaporation of the methanol the remainder is taken up in 150 ml of ice water and made strongly acidic with conc. hydrochloric acid. After saturation with common salt the hydrochloride precipitated is suction filtered, the mother liquor is made strongly alkaline with 6N sodium hydroxide solution, extracted with ethyl acetate, dried and evaporated down. The hydrochloride precipitated is suspended in a mixture of water and ethyl acetate and, under cooling, made strongly alkaline with 6N sodium hydroxide solution. The ethyl acetate phase is washed with water and saturated saline solution, dried and evaporated down. Crystallisation of the residue from petroleum ether yields 15.1 g trans-N-methyl-4-phenylcyclohexylamine (colourless crystals). The petroleum ether mother liquor is evaporated down and combined with the evaporation residue from the hydrochloride precipitation. Separation on aluminium oxide (activity stage III, ethyl acetate/petroleum ether=1:1 to 2:1, v:v) yields 2.4 g cis-N-methyl-4-phenylcyclohexylamine,

Workup

  1. filtrationAfter filtering
  2. concentrationconcentration
  3. customby evaporation the residue
  4. dissolutionis dissolved in 200 ml of methanol and at −20° C
  5. addition7.8 g sodium borohydride are added batchwise
  6. additionall been added the mixture
  7. customAfter evaporation of the methanol the remainder
  8. customAfter saturation with common salt the hydrochloride precipitated
  9. filtrationfiltered
  10. extractionextracted with ethyl acetate
  11. customdried
  12. customevaporated down
  13. customThe hydrochloride precipitated
  14. additionis suspended in a mixture of water and ethyl acetate
  15. temperatureunder cooling
  16. washThe ethyl acetate phase is washed with water and saturated saline solution
  17. customdried
  18. customevaporated down
  19. customCrystallisation of the residue from petroleum ether

Sources & evidence

ORD record
ord-3a8d5d4f0abd465d8da62b9d93084d70
Source dataset
uspto-grants-2002_02
Patent number
US06346545B1

Reaction notes

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