Aluminium lithium hydride → N-((1-Benzylpiperidin-4-yl)methyl)ethanamine

HRID 361840Notes

Reaction equation

HRID 361840 reaction equation
[CH2:1]([NH:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:12]([N:9]1[CH2:10][CH2:11][CH:6]([CH2:4][NH:3][CH2:1][CH3:2])[CH2:7][CH2:8]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 272346131-benzyl-N-ethylpiperidine-4-carboxamide

Product 1

HCID 54124174N-((1-Benzylpiperidin-4-yl)methyl)ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Ethyl-1-benzyl-4-piperidinyl carboxamide (EXAMPLE 174, 8.03 g, 32.60 mmol) is dissolved in THF and cooled to 0°. Lithium aluminum hydride (1M in THF) is added dropwise. The solution is refluxed 4.5 hr, then quenched at 0° by adding 1.24 ml water, 1.24 ml 15% aqueous sodium hydride, and 3.71 ml water. Filtration through a pad of diatomaceous earth and sodium sulfate and then evaporation of the solvent gives the title compound; NMR (300 MHz, CDCl3) 7.14, 3.32, 2.73, 2.50, 2.35, 1.79, 1.55, 1.34, 1.12 and 0.97δ.

Workup

  1. temperaturecooled to 0°
  2. temperatureThe solution is refluxed 4.5 hr
  3. customquenched at 0°
  4. additionby adding 1.24 ml water, 1.24 ml 15% aqueous sodium hydride, and 3.71 ml water
  5. filtrationFiltration through a pad of diatomaceous earth and sodium sulfate
  6. customevaporation of the solvent

Sources & evidence

ORD record
ord-ded7ec95038b4a8fb18c2adc04b3f2b2
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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