1-Methyl-4-phenylpiperidine-4-carbonitrile → (1-Methyl-4-phenylpiperidin-4-yl)methanamine

HRID 1800812Notes

Reaction equation

HRID 1800812 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:8]#[N:9])[CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:8][NH2:9])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 625131-Methyl-4-phenylpiperidine-4-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 343885(1-Methyl-4-phenylpiperidin-4-yl)methanamineYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-methyl-4-phenylpiperidine-4-carbonitrile (1.0 g, 4.99 mmol) in THF (25 mL) was slowly added to a suspension of LAH (0.379, 9.99 mmol) in THF (10 mL). The reaction was stirred for 2 hours and then quenched with sodium sulfate decahydrate. This was stirred for 30 minutes, and then ethyl acetate was added. The mixture was stirred 10 minutes, and then filtered on celite. The filtrate was concentrated on rotovap to give the desired compound (0.916 g, 96%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm: 1.79-1.89 24H, m), 2.18-2.28 (7H, m), 2.55-2.65 (2H, m), 2.77 (2H, s), 7.21-7.27 (1H, m), 7.28-7.39 (4H, m).

Workup

  1. customquenched with sodium sulfate decahydrate
  2. stirringThis was stirred for 30 minutes
  3. additionethyl acetate was added
  4. stirringThe mixture was stirred 10 minutes
  5. filtrationfiltered on celite
  6. concentrationThe filtrate was concentrated on rotovap

Sources & evidence

ORD record
ord-f28a7e161f9c4ecebd869b43a25ce4da
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

Loading…