Water → HCID 14032622, compound

HRID 986129Notes

Reaction equation

HRID 986129 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.ClCCl.CO>[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

7

Reactant 4

HCID 962Water2×HCID 24758Sodium hydrideHCID 86134770HCID 86134770, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14032622HCID 14032622, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

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 chromatogrphed 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. customThe appropriate fractions were evaporated
  9. customThe residue was recrystallized twice from isopropyl alcohol-water (one charcoal treatment)

Sources & evidence

ORD record
ord-657dd85368f94896870fbf0538adafcb
Source dataset
uspto-grants-1987_12
Patent number
US04710573

Reaction notes

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