Water → HCID 14032622, compound

HRID 867694Notes

Reaction equation

HRID 867694 reaction equation
[C:1]1([NH:7][N:8]=[C:9]([CH:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:26])[CH3:25])[CH2:20][CH2:19]2)[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2F)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].O>CN(C)C=O>[C:24]([N:21]1[CH2:22][CH2:23][CH:18]([C:9]2[C:10]3[C:15](=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=2)[CH2:19][CH2:20]1)(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 86134770HCID 86134770, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14032622HCID 14032622, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3.0 g of 1-acetyl-4-(2,4-difluorobenzoyl)piperidine phenylhydrazone in 30 ml of dimethylformamide, under nitrogen, was added 0.44 g of a 50% oil dispersion of sodium hydride. The reaction mixture was heated, and at about 40° C. a vigorous evolution of hydrogen occurred. The temperature was then raised to 80° C. and held there for 1.5 hrs. The reaction mixture was poured into water and the aqueous suspension was extracted with ethyl acetate. The ethyl acetate extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated to yield an oil. The oil was combined with the oil from another experiment and a total of 13.5 g of material was chromatographed on a Water's Prep LC 500. Two silica gel columns were utilized and dichloromethane-methanol (3%) was used as the eluent. The appropriate fractions were evaporated. The residue was recrystallized twice from isopropyl alcohol-water (one charcoal treatment) to yield 2.4 g (18%) of product, mp 126°-128° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. customat about 40° C.
  3. extractionthe aqueous suspension was extracted with ethyl acetate
  4. washThe ethyl acetate extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto yield an oil
  8. customa total of 13.5 g of material was chromatographed on a Water'
  9. customThe appropriate fractions were evaporated
  10. customThe residue was recrystallized twice from isopropyl alcohol-water (one charcoal treatment)

Sources & evidence

ORD record
ord-a6361ec12317496ab109f36f8d69b57e
Source dataset
uspto-grants-1988_10
Patent number
US04775761

Reaction notes

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