Sodium hydride → HCID 68714062, compound

HRID 2239356Notes

Reaction equation

HRID 2239356 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH2:9][OH:10])([CH3:8])[CH2:3]1.[H-].[Na+].F[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18]>CN(C=O)C>[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH2:9][O:10][C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]#[N:18])([CH3:8])[CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 678803-FluorobenzonitrileHCID 44827703(1,3-Dimethylpiperidin-3-yl)methanol

Product 1

HCID 68714062HCID 68714062, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (1,3-dimethylpiperidin-3-yl)methanol (0.50 g, 3.5 mmol) in dry DMF (10 mL) at room temperature, 60% sodium hydride in oil (0.28 g, 7.0 mmol) was added. The reaction mixture was stirred at room temperature for 5 minutes and 3-fluoro benzonitrile (0.44 g, 3.7 mmol) was added. Due to excessive foaming the reaction mixture was diluted with dry DMF to 15 mL. The reaction mixture was then stirred at room temperature over night and quenched with water. The product was extracted with EtOAc and the organic layer was dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography using a gradient with EtOAc:MeOH:TEA (1:0.1:0.05) in EtOAc, which gave the product as a colorless oil. Yield: 0.53 g (59%). 1H NMR (400 MHz, CD3OD) δ 7.41 (t, 1H, J=8.11 Hz), 7.20-7.27 (m, 3H), 3.89 (d, 1H, J=8.89 Hz), 3.82 (d, 1H, J=8.89 Hz), 2.21-2.51 (m, 3H), 2.19 (s, 3H), 2.12 (m, 1H), 1.54-1.67 (m, 3H), 1.21-1.30 (m, 1H), 1.07 (s, 3H).

Workup

  1. stirringThe reaction mixture was then stirred at room temperature over night
  2. customquenched with water
  3. extractionThe product was extracted with EtOAc
  4. dry with materialthe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-78a1ac97fba6454ab93048b247b71b08
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

Loading…