Water → 2-[(1-Methyl-4-piperidinyl)oxy]-3-pyridinecarbonitrile

HRID 645545Notes

Reaction equation

HRID 645545 reaction equation
F[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][N:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1.[H-].[Na+].O>CN(C)C=O>[CH3:10][N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:2]2[N:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 660484-Piperidinol, 1-methyl-HCID 27832543-Cyano-2-fluoropyridine

Product 1

HCID 612834102-[(1-Methyl-4-piperidinyl)oxy]-3-pyridinecarbonitrileYield 29.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-fluoro-nicotinonitrile (400 mg, 3.3 mmol) and 1-methyl-piperidin-4-ol (380 mg, 3.3 mmol) in N,N-dimethylformamide (30 mL) was added NaH (60%) (160 mg, 4.0 mmol) in portions. The reaction was stirred overnight at rt. The mixture was poured into water, and extracted with ethyl acetate (2×). The solvent was removed, and the resulting residue was chromatographed using ethyl acetate/methanol (8:1) to give the title compound (210 mg, 29%). MS (DCI/NH3) m/z 218 (M+1)+

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. customThe solvent was removed
  3. customthe resulting residue was chromatographed

Sources & evidence

ORD record
ord-3fd854ad98a84f538bfae772a6740f50
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

Loading…