Cyclohexanone → 1-[1-(Piperidin-1-yl)cyclohexyl]methanamine

HRID 2071987Notes

Reaction equation

HRID 2071987 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C-:8]#[N:9].[K+].[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>O.C(O)C>[NH2:9][CH2:8][C:11]1([N:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 9032Potassium CyanideHCID 2723721Piperidine, hydrochloride (1:1)

Product 1

HCID 3984021-[1-(Piperidin-1-yl)cyclohexyl]methanamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Piperidine hydrochloride (24.1 g 0.2 mole) and KCN (13.0 g. 0.2 mole) were dissolved in water (80 ml) and ethanol (160 ml). To this stirred solution was added dropwise a solution of cyclohexanone (19.6 g., 0.2 mole) in ethanol (40 ml), the mixture refluxed for 24 hr. Ethanol was then removed under reduced pressure and the residue extracted with chloroform. The extract was washed with water, dried (Na2SO4) and evaporated under reduced pressure to give a pale, amber oil (27.0 g. 68.8%) which crystallised on standing. Recrystallisation from ethanol afforded colourless plates of 1-(1-cyanocyclohexyl)piperidine m.p. 67°-8°.

Workup

  1. temperaturethe mixture refluxed for 24 hr
  2. customEthanol was then removed under reduced pressure
  3. extractionthe residue extracted with chloroform
  4. washThe extract was washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customto give a pale, amber oil (27.0 g. 68.8%) which
  8. customcrystallised
  9. customRecrystallisation from ethanol afforded colourless plates of 1-(1-cyanocyclohexyl)piperidine m.p. 67°-8°

Sources & evidence

ORD record
ord-9d40dbd680bf4faaa4cde7feaa4dc57f
Source dataset
uspto-grants-1977_09
Patent number
US04049663

Reaction notes

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