Dimethylformamide → HCID 19366931, compound

HRID 1737439Notes

Reaction equation

HRID 1737439 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[C:11]1([CH2:18][OH:19])[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1.CN([CH:23]=[O:24])C>CCCCCC>[F:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[C:11]1([C:18]([O:24][CH3:23])=[O:19])[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 19367002HCID 19367002, compound

Product 1

HCID 19366931HCID 19366931, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
90 °C

Procedure

NaH (158 mg, 6.56 mmol) was added to 4-(2,5-difluorophenyl)-4-hydroxymethyl-1-methylpiperidine (1.45 g, 6.56 mmol) in DMF (20 mL). The slurry was heated to 90° C. for 6 h. The reaction was diluted with hexane (200 mL), washed with water (200 mL), brine (50 mL), dried (MgSO4), and concentrated to yield 1.21 g (92%) of the title compound as a white crystalline solid; 1H NMR (400 MHz, CDCl3) δ 6.98 (dd, 1H), 6.54 (dt, 1H), 6.48 (dd, 1H), 4.37 (s, 2H), 2.84 (m, 2H), 2.31 (s, 3H), 1.97 (4H, pentuplet), 1.71 (m, 2H) ppm.

Workup

  1. washwashed with water (200 mL), brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4d44ed8eb1c544b39c2ef3e62b983734
Source dataset
uspto-grants-1999_10
Patent number
US05962462

Reaction notes

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