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

HRID 1800814Notes

Reaction equation

HRID 1800814 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[CH2:9][CH2:10][C:11]([CH2:14][NH2:15])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13]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-methylamineYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

A suspension of 1-benzyl-4-phenylpiperidine-4-carbonitrile (2.0 g, 6.39 mmol) in THF (25 mL) was slowly added to a suspension of lithium aluminum hydride (0.340 g, 8.95 mmol) in THF (10 mL) and the reaction was stirred at 23° C. for 3 hours. The reaction was then quenched with sodium sulfate decahydrate and stirred for 30 minutes. Ethyl acetate was added and the reaction was stirred for 10 more minutes, and then filtered on celite. The filtrate was concentrated to give an oil (1.45 g, 81%) which was used as such for the next reaction. 1H NMR (400 MHz, CDCl3) δ ppm: 1.81-1.91 (2H, m), 2.23-2.28 (4H, m), 2.65-2.67 (2H, m), 2.78 (2H, s), 3.45 (2H, s), 7.23-7.34 (8H, m), 7.36-7.41 (2H, m).

Workup

  1. customThe reaction was then quenched with sodium sulfate decahydrate
  2. stirringstirred for 30 minutes
  3. additionEthyl acetate was added
  4. stirringthe reaction was stirred for 10 more minutes
  5. filtrationfiltered on celite
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ba5cfe64477c476bba53afde47010825
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

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