HCID 68714062, compound → HCID 68709013, compound

HRID 2239357Notes

Reaction equation

HRID 2239357 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])([CH3:8])[CH2:3]1>CO.[Ni]>[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH2:14][NH2:15])[CH:16]=[CH:17][CH:18]=2)([CH3:8])[CH2:3]1

Participants

4

Reactant 1

HCID 68714062HCID 68714062, compound

Product 1

HCID 68709013HCID 68709013, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

3-[(1,3-Dimethylpiperidin-3-yl)methoxy]benzonitrile (0.53 g, 2.2 mmol) was dissolved in MeOH (30 mL)/NH3(sat) (0.05M) and hydrogenated over a Raney Nickel CatCart (30×4 mm) using the H-Cube system at 50 bar and 50° C. at a flow rate of 1 mL/min. LC-MS showed <100% conversion so the process was repeated. The reaction mixture was concentrated and dried in vacuo, which gave the product as a clear oil. Yield: 0.48 g (90%). 1H NMR (400 MHz, CD3OD) δ 7.13 (t, 1H, J=8.12 Hz), 6.85 (s, 1H), 6.80 (d, 1H, J=7.61 Hz), 6.72 (d, 1H, J=7.61 Hz), 3.74 (m, 2H), 3.67 (s, 2H), 3.23 (s, 2H), 2.04-2.43 (m, 7H), 1.48-1.63 (m, 3H), 1.20 (m, 1H), 1.02 (s, 3H).

Workup

  1. customat 50 bar and 50° C.
  2. concentrationThe reaction mixture was concentrated
  3. customdried in vacuo, which

Sources & evidence

ORD record
ord-47e410f07190419184b95233cb38aa34
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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