Water → N-Ethyl-1-(1-piperidinyl)cyclohexanemethanamine

HRID 1283535Notes

Reaction equation

HRID 1283535 reaction equation
[C:1]([NH:4][CH2:5][C:6]1([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:1]([NH:4][CH2:5][C:6]1([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 21409872HCID 21409872, compound

Product 1

HCID 21409821N-Ethyl-1-(1-piperidinyl)cyclohexanemethanamineYield 67.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-[1-(acetamidomethyl)cyclohexyl] piperidine (5.5 g.) in dry tetrahydrofuran (50 ml) was added dropwise with stirring during 10 mins. to a suspension of lithium aluminium hydride (3.8 g.) in dry tetrahydrofuran (100 ml). The mixture was heated under reflux for 51/2 hrs. and stirred at room temperature for 16 hrs. Water (10 ml) was added dropwise to decompose excess lithium aluminium hydride (grey suspension had turned white). The suspension was filtered through hyflo, washed with ether and the combined filtrates dried (anhyd. Na2SO4). The dried filtrate was evaporated to dryness under reduced pressure and the residual oil (5 g.) was distilled under high vacuum to give 1-[1-(Ethylaminomethyl)cyclohexyl]piperidine (3.5 g.). b.p. C 138°-144° at 5.5 mm.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 51/2 hrs
  3. stirringand stirred at room temperature for 16 hrs
  4. filtrationThe suspension was filtered through hyflo
  5. washwashed with ether
  6. dry with materialthe combined filtrates dried (anhyd. Na2SO4)
  7. customThe dried filtrate was evaporated to dryness under reduced pressure
  8. distillationthe residual oil (5 g.) was distilled under high vacuum

Sources & evidence

ORD record
ord-f6cc3bf129f144f9b14d24358f3f93e9
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

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