1-Benzyl-4-cyano-4-phenylpiperidine → 1-Benzyl-4-phenylpiperidine-4-methylamine

HRID 380571Notes

Reaction equation

HRID 380571 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:14]#[N:15])[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-]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:14][NH2:15])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1914081-Benzyl-4-cyano-4-phenylpiperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 8042381-Benzyl-4-phenylpiperidine-4-methylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.5 g of 1-N-Benzyl-4-phenyl-4-cyanopiperidine (16.3 mmol, Fisher Scientific) in 50 mL of THF was added 49 mL of lithium aluminum hydride (1 M in THF, 49 mmol) and the reaction mixture was stirred for 12 hr at rt. The reaction was quenched by the addition of 5 mL of water, 5 mL of 15% solution of NaOH followed by 5 mL of water. The organic fraction was dried over MgSO4, filtered and the filtrate was concentrated to give the title compound which was used without further purification.

Workup

  1. customThe reaction was quenched by the addition of 5 mL of water, 5 mL of 15% solution of NaOH
  2. dry with materialThe organic fraction was dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7079a6953cbd4fa9a613a6bb41b9e65a
Source dataset
uspto-grants-2001_10
Patent number
US06303637B1

Reaction notes

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