Water → HCID 61283411, compound

HRID 645544Notes

Reaction equation

HRID 645544 reaction equation
F[C:2]1[CH: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>O1CCOCC1>[CH3:10][N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:2]2[CH: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 678552-Fluorobenzonitrile

Product 1

HCID 61283411HCID 61283411, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 2-fluoro-benzonitrile (1.6 g, 13.2 mmol) and 1-methyl-piperidin-4-ol (1.52 g, 13.2 mmol) in dioxane (50 mL) was added NaH (60%) (634 mg, 15.8 mmol) in portion. The reaction was heated at 50° C. overnight. The mixture was poured into water, and extracted with ethyl acetate (2×). The solvent was removed, and the resulting residue was chromatographered using ethyl acetate/methanol (20:1-10:1) to give the title compound (870 mg, 31%). MS (DCI/NH3) m/z 217 (M+1)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.63 (m, 2H) 1.86 (m, 2H) 2.11 (s, 3H) 2.18 (m, 2H) 2.48 (m, 2H) 4.55 (m, 1H) 7.00 (td, J=7.67, 0.61 Hz, 1H) 7.23 (d, J=8.59 Hz, 1H) 7.56 (td, J=10.13, 7.36, 1.84 Hz, 1H) 7.63 (dd, J=7.67, 1.84 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-ccf5b4b69c9545449a260d9120ce2f98
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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