Ammonia → 1-(Cyclohexylmethyl)piperidin-4-amine

HRID 261049Notes

Reaction equation

HRID 261049 reaction equation
[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:15]>[Ni]>[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH2:15])[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 119596651-(Cyclohexylmethyl)piperidin-4-one

Product 1

HCID 64969411-(Cyclohexylmethyl)piperidin-4-amine

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A solution of 1-cyclohexylmethylpiperid-4-one (65 g; 0.33 moles in a saturated ethanolic solution of ammonia (350 ml) was hydrogenated in the presence of Raney nickel catalyst (6.5 g) at 75° C. and 13 atmospheres for 3.5 hours. The mixture was cooled, the catalyst filtered off and the solvent removed by distillation in vacuo. The residue was treated with a saturated ethanolic solution of hydrogen chloride, and the insoluble dihydrochloride was filtered off, treated with an aqueous solution of sodium hydroxide and extracted with chloroform. The organic layer was dried (Na2SO4) and the solvent removed in vacuo giving 1-cyclohexylmethyl-4-aminopiperidine (45.5 g) as a viscous liquid, b.p. 105°-110° C./0.3 mm Hg.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe catalyst filtered off
  3. customthe solvent removed by distillation in vacuo
  4. additionThe residue was treated with a saturated ethanolic solution of hydrogen chloride
  5. filtrationthe insoluble dihydrochloride was filtered off
  6. additiontreated with an aqueous solution of sodium hydroxide
  7. extractionextracted with chloroform
  8. dry with materialThe organic layer was dried (Na2SO4)
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-5ead671b13004a0ba7607c817d8df21a
Source dataset
uspto-grants-1979_08
Patent number
US04163789

Reaction notes

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