(S)-3-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yl)propanenitrile → (S)-3-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yl)propan-1-amine

HRID 874071Notes

Reaction equation

HRID 874071 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][C:15]#[N:16])[CH:10]=[N:11][CH:12]=1.[H][H]>[Ni].N.CO>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][NH2:16])[CH:10]=[N:11][CH:12]=1

Participants

6

Reactant 2

HCID 86659933(S)-3-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yl)propanenitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 54675475(S)-3-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yl)propan-1-amineYield 88.4%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

(S)-3-(5-(1-Methylpyrrolidin-2-yl)pyridin-3-yl)propanenitrile (preparation 3) (140 mg, 0.65 mmol) and Raney nickel (50 mg) in 20% ammonia in MeOH (50 mL) were stirred under 50 psi hydrogen at 50° C. for 4 hours. The reaction mixture was filtered through Celite then the solvent evaporated. The crude product was purified by flash chromatography (7% [20% ammonia in MeOH] in DCM) to give the title compound as a pale yellow oil (126 mg, 88%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent evaporated
  3. customThe crude product was purified by flash chromatography (7% [20% ammonia in MeOH] in DCM)

Sources & evidence

ORD record
ord-6285b9c1f8be41ce9bcf0121d2b104c1
Source dataset
uspto-grants-2015_03
Patent number
US08980276B2

Reaction notes

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