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

HRID 867704Notes

Reaction equation

HRID 867704 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-a5bb8584e2dc4d778f029da3b532860d
Source dataset
uspto-grants-1988_10
Patent number
US04775761

Reaction notes

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