Hydrazine hydrate (1:1) → HCID 178477868, compound

HRID 845631Notes

Reaction equation

HRID 845631 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2F)[CH2:6][CH2:5]1)(=O)C.O.[NH2:21][NH2:22]>C(O)CCC>[Cl:17][C:14]1[CH:13]=[C:12]2[C:11]([C:10]([CH:7]3[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]3)=[N:21][NH:22]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 23048180HCID 23048180, compound

Product 1

HCID 178477868HCID 178477868, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 18.0 g of 1-acetyl-4-(4-chloro-2-fluorobenzoyl)piperidine, 130 ml of n-butanol and 51 ml of hydrazine monohydrate was stirred under reflux for 48 hrs. Most of the n-butanol was evaporated in vacuo and the residue was diluted with water. The aqueous mixture was extracted with ethyl acetate, and the extract was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from acetonitrile to yield 3.0 g (20%) of product. This product was combined with a 1.3 g sample from another experiment and the combined samples (4.3 g) were recrystallized from acetonitrile to yield the analytical sample, mp 174-176° C.

Workup

  1. temperatureunder reflux for 48 hrs
  2. customMost of the n-butanol was evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionThe aqueous mixture was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d32ce60e6efe47b5b814efc89d8eea15
Source dataset
uspto-grants-1988_07
Patent number
US04758668

Reaction notes

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