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

HRID 261048Notes

Reaction equation

HRID 261048 reaction equation
[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11](=[N:14]O)[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 203958701-Cyclohexylmethylpiperid-4-one oximeHCID 21226445Aluminium lithium hydride

Product 1

HCID 64969411-(Cyclohexylmethyl)piperidin-4-amineYield 87.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-cyclohexylmethylpiperid-4-one oxime (37.8 g; 0.18 moles) dissolved in anhydrous diethyl ether (250 ml) was added little by little to a suspension of lithium aluminium hydride (14.04 g; 0.36 moles) in anhydrous diethyl ether (200 ml). On completion of the addition, the resultant mixture was heated to the boiling point and maintained there under reflux for 12 hours, and then thoroughly cooled whilst water (14 ml), 15% (w/v) aqueous sodium hydroxide solution (14 ml) and water (42 ml) were added successively. The mixture was filtered and the ethereal solution was dried (Na2SO4) and the solvent removed in vacuo. The product 1-cyclohexylmethyl-4-aminopiperidine (31 g) was isolated as a viscous liquid, b.p. 105°-110° C./0.3 mm Hg.

Workup

  1. additionwas added little by
  2. additionOn completion of the addition
  3. temperaturemaintained there
  4. temperatureunder reflux for 12 hours
  5. filtrationThe mixture was filtered
  6. dry with materialthe ethereal solution was dried (Na2SO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-47515e19b24148ee86ac50b0b78c1b3d
Source dataset
uspto-grants-1979_08
Patent number
US04163789

Reaction notes

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