HCID 57619655, compound → 3-(1-Methyl-piperidin-4-yloxy)-benzylamine

HRID 2239322Notes

Reaction equation

HRID 2239322 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[CH2:4][CH2:3]1>N.CO.[Ni]>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH2:12][NH2:13])[CH2:4][CH2:3]1

Participants

5

Reactant 1

HCID 57619655HCID 57619655, compound

Product 1

HCID 392028503-(1-Methyl-piperidin-4-yloxy)-benzylamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

3-(1-Methyl-piperidin-4-yloxy)-benzonitrile (1.20 g, 5.55 mmol) was dissolved (0.05 M) in NH3 in MeOH (111 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 a light orange oil. Yield: 1.16 g (95%). 1H NMR (400 MHz, CDCl3) δ 7.25-7.17 (m, 1H), 8-6.83 (m, 2H), 6.78-6.73 (dd, J=7.67 Hz, J=2.05 Hz), 4.32 (m, 1H), 3.80 (s, 2H), δ 2.69 (m, 2H), 2.36-2.25 (m, 5H), 2.05-1.95 (m, 2H), 1.88-1.72 (m, 4H). MS (ESI+) 221.1 (M+1H+).

Workup

  1. customEvaporation in vacuo
  2. customyielded a light orange oil

Sources & evidence

ORD record
ord-44713924e4d84d8292696ccc0ce7fb95
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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