6-[(1-Methylpiperidin-4-yl)oxy]pyridine-2-carbonitrile → 1-{6-[(1-Methylpiperidin-4-yl)oxy]pyridin-2-yl}methanamine

HRID 2239337Notes

Reaction equation

HRID 2239337 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[N:14]=[C:13]([C:15]#[N:16])[CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1>N.[Ni]>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:8][C:9]2[N:14]=[C:13]([CH2:15][NH2:16])[CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 645945946-[(1-Methylpiperidin-4-yl)oxy]pyridine-2-carbonitrile

Product 1

HCID 622878781-{6-[(1-Methylpiperidin-4-yl)oxy]pyridin-2-yl}methanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

6-[(1-Methylpiperidin-4-yl)oxy]pyridine-2-carbonitrile (1.62 g, 7.46 mmol, from step a above) was dissolved in 150 mL of ammonia saturated MeOH and hydrogenation was performed using a Raney-Ni 30×4 mm CatCart (H-Cube, 50 bar, 50° C., 1 mL/min). The mixture was evaporated and was pure enough to use directly in the next step below. Yield: 1.62 g (98%). 1H NMR (500 MHz, CDCl3) δ 7.50 (m, 1H), 6.75 (d, 1H), 6.56 (d, 1H), 5.11 (m, 1H), 3.82 (s, 2H), 2.74 (m, 2H), 2.43-2.30 (m, 5H, thereof a singlet at 2.34), 2.07 (m, 2H), 1.87 (m, 2H).

Workup

  1. customThe mixture was evaporated

Sources & evidence

ORD record
ord-ddf0e15641024f4ea13d0a9a7351b332
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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