HCID 21959661, compound → HCID 21959563, compound

HRID 2239348Notes

Reaction equation

HRID 2239348 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][N:16]=2)[C:12]#[N:13])[CH2:4][CH2:3]1>N.[Ni]>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:8][C:9]2[CH:10]=[C:11]([CH2:12][NH2:13])[CH:14]=[CH:15][N:16]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 21959661HCID 21959661, compound

Product 1

HCID 21959563HCID 21959563, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

2-[(1-Methylpiperidin-4-yl)oxy]isonicotinonitrile (0.250 g, 1.51 mmol, from step a above) was dissolved in 10 mL of ammonia saturated MeOH and 0.200 g Raney Nickel was added. The mixture was hydrogenated at 5 atm overnight. The mixture was filtered and evaporated to give 0.242 g (95%) of crude product which was used in the following step. 1H NMR (300 MHz, CD3OD) δ 8.01 (d, 1H), 6.89 (d, 1H), 6.76 (bs, 1H), 5.00 (m, 1H), 3.77 (bs, 2H), 2.73 (m, 2H), 2.37 (m, 2H), 2.30 (s, 3H), 2.03 (m, 2H), 1.81 (m, 2H).

Workup

  1. customwas hydrogenated at 5 atm overnight
  2. filtrationThe mixture was filtered
  3. customevaporated

Sources & evidence

ORD record
ord-4bf3a718fd4c4839a1ab7720e4bfa704
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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