Water → (1-Phenylpiperidin-4-YL)methanamine

HRID 963999Notes

Reaction equation

HRID 963999 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][CH:10]([C:13]([NH2:15])=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:1]1([N:7]2[CH2:8][CH2:9][CH:10]([CH2:13][NH2:15])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 105843391-Phenylpiperidine-4-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 10607720(1-Phenylpiperidin-4-YL)methanamineYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Phenylpiperidine-4-carboxamide (1.5 g) was added portionwise to a stirring suspension of lithium aluminium hydride (0.5 g) in dry tetrahydrofuran (100 ml) under nitrogen. The resulting suspension was stirred at ambient termperature for 2 hours, then heated under reflux for 2 hours. The mixture was cooled, and water (0.5 ml), then concentrated sodium hydroxide solution (0.5 ml) were added. The resulting precipitate was removed by filtration (Celite). The filtrate was dried over magnesium sulphate, and the solvent removed in vacuo to yield 1-(1-phenylpiperid-4-yl)methylamine (1.15 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe mixture was cooled
  4. customThe resulting precipitate was removed by filtration (Celite)
  5. dry with materialThe filtrate was dried over magnesium sulphate
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1e24d108709346ccad5ccc2107c6ecb9
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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