3-[(1-Methylpiperidin-3-yl)oxy]benzonitrile → 1-{3-[(1-Methylpiperidin-3-yl)oxy]phenyl}methanamine

HRID 2239340Notes

Reaction equation

HRID 2239340 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[CH2:3]1>N.CO.[Ni]>[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([O:8][C:9]2[CH:10]=[C:11]([CH2:12][NH2:13])[CH:14]=[CH:15][CH:16]=2)[CH2:3]1

Participants

5

Reactant 1

HCID 687117213-[(1-Methylpiperidin-3-yl)oxy]benzonitrile

Product 1

HCID 687098241-{3-[(1-Methylpiperidin-3-yl)oxy]phenyl}methanamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

3-[(1-Methylpiperidin-3-yl)oxy]benzonitrile (623 mg, 2.90 mmol) was dissolved (0.05 M) in NH3 in MeOH (58 ml). Hydrogenation was performed using a Raney-Ni 30×4 mm CatCart (H-Cube, 50 bar, 50° C., 1 ml/min). Evaporation in vacuo yielded the title compound as a colorless oil. Yield: 633 mg (99%). 1H NMR (400 MHz, CDCl3) δ 7.20 (t, 1H, J=7.9 Hz), 6.89-6.83 (m, 2H), 6.79 (dd, 1H, J=8.2 Hz, J=2.2 Hz), 4.37 (m, 1H, J=4.2 Hz), 3.80 (s, 2H), 2.91 (d, 1H), 2.62-2.54 (m, 1H), 2.28 (s, 3H), 2.13 (m, 2H), 1.97 (m, 1H), 1.86-1.76 (m, 1H), 1.69-1.54 (m, 3H), 1.52-1.40 (m, 1H).

Workup

  1. customEvaporation in vacuo

Sources & evidence

ORD record
ord-4b1cb40a066f4b7ba90fa06c5bb79403
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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