1-Butanol → HCID 178505426, compound

HRID 867686Notes

Reaction equation

HRID 867686 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2F)[CH2:6][CH2:5]1)(=O)C.O.[NH2:21][NH2:22].C(O)CCC>O>[F: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

5

Reactant 3

HCID 2631-ButanolHCID 24654Hydrazine hydrate (1:1)HCID 27407071-Acetyl-4-(2',4'-difluorobenzoyl)piperidine

Product 1

HCID 178505426HCID 178505426, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 20.0 g of 1-acetyl-4-(2,4-difluorobenzoyl)-piperidine, 60 ml of hydrazine hydrate and 150 ml of n-butanol was refluxed for 48 hrs. The reaction was poured into 11 of water, and the mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was evaporated in vacuo. Recrystallization of the residue from isopropanol-water and then from isopropanol yielded 3.3 g (20.1%) of product, mp 214°-216° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customRecrystallization of the residue from isopropanol-water

Sources & evidence

ORD record
ord-69eeb73ffa284d8fafcd456078e2d965
Source dataset
uspto-grants-1988_10
Patent number
US04775761

Reaction notes

Loading…