Water → (1-Benzyl-4-piperidyl)methanamine

HRID 1059344Notes

Reaction equation

HRID 1059344 reaction equation
[CH2:1]([N:8]1[CH2:16][CH2:15][CH:11]([C:12]([NH2:14])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[NH2:14][CH2:12][CH:11]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 7831561-Benzylpiperidine-4-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 1514444(1-Benzyl-4-piperidyl)methanamineYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2.2 g of 1-benzylisonipecotamide in 50 ml of tetrahydrofuran was added 1.58 g of lithium aluminum hydride at 0° C. and the resulting mixture was heated under reflux for 2 hours. Then the reaction mixture was cooled to 0° C. After adding water and a 10% aqueous solution of sodium hydroxide, the insoluble matters were filtered off. After distilling off the solvent under reduced pressure, 2.0 g of the title compound was obtained as a brown oily substance.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. filtrationa 10% aqueous solution of sodium hydroxide, the insoluble matters were filtered off
  4. distillationAfter distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-f30603b999a249339e022598a7aa2c68
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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