Sodium hydride → HCID 68710696, compound

HRID 2239342Notes

Reaction equation

HRID 2239342 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1.[H-].[Na+].F[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17]>CN(C=O)C>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 678803-FluorobenzonitrileHCID 2719711-Methyl-4-piperidinemethanol

Product 1

HCID 68710696HCID 68710696, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(1-Methylpiperidin-4-yl)methanol (0.500 g, 3.87 mmol) was dissolved in dry DMF (8 mL), cooled (<0° C.), NaH (0.232 g, 5.80 mmol, 55% in oil) added and stirred for 30 minutes. 3-fluorobenzonitrile (0.492 g, 4.06 mmol) was added and the reaction mixture allowed to warm to r.t. over 1 hour. Due to excessive foaming the reaction mixture was diluted with dry DMF to 20 mL and stirred over night at r.t. The reaction was quenched by addition of water portionwise, and the mixture was extracted with EtOAc. The organics were dried (MgSO4) and concentrated in vacuo. The product was purified by flash chromatography using a step gradient of EtOAc:MeOH:TEA (100:10:2) in EtOAc to give the title compound as an oil. Yield: 0.417 g (44%). 1H NMR (400 MHz, CDCl3) δ 7.29-7.35 (m, 1H), 7.19 (m, 1H), 7.05-7.10 (m, 2H), 3.78 (d, 2H, J=6.1 Hz), 2.83-2.90 (m, 2H), 2.26 (s, 3H), 1.89-1.98 (m, 2H), 1.70-1.84 (m, 3H), 1.33-1.46 (m, 2H).

Workup

  1. additionadded
  2. stirringstirred over night at r.t
  3. customThe reaction was quenched by addition of water portionwise
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialThe organics were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-90df9daddb8b43b09606bcf179a0161f
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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