HCID 68710696, compound → HCID 68710204, compound

HRID 2239343Notes

Reaction equation

HRID 2239343 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])[CH2:4][CH2:3]1>[Ni]>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH2:13][NH2:14])[CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 1

HCID 68710696HCID 68710696, compound

Product 1

HCID 68710204HCID 68710204, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

3-[(1-Methylpiperidin-4-yl)methoxy]benzonitrile (0.417 g, 1.81 mmol) was dissolved in MeOH/NH3(sat) (0.05M) and hydrogenated over a Raney Nickel CatCart (30×4 mm) using the H-Cube system (50 bar, 50° C., 1 mL/min). The product was concentrated and dried in vacuo, to give the title compound as an oil. Yield: 0.371 g (87%). 1H NMR (400 MHz, CD3OD) δ 7.18 (t, 1H, J=8.1 Hz), 6.83-6.89 (m, 2H), 6.75 (dd, 1H, J=8.1 Hz, J=2.1 Hz), 4.82 (s, 2H), 3.80 (d, 2H, J=6.1 Hz), 3.71 (s, 2H), 2.84-2.91 (m, 2H), 2.46 (s, 3H), 1.97-2.06 (m, 2H), 1.79-1.87 (m, 2H), 1.70-1.79 (m, 1H), 1.33-1.46 (m, 2H).

Workup

  1. customthe H-Cube system (50 bar, 50° C., 1 mL/min)
  2. concentrationThe product was concentrated
  3. customdried in vacuo

Sources & evidence

ORD record
ord-b1ea86b206864db2bc54f8b760126f8d
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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