1-Butanol → HCID 178505426, compound

HRID 1382558Notes

Reaction equation

HRID 1382558 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 1 l 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-848d0ff24e0e4ef7ba7bbb07c8a7bd82
Source dataset
uspto-grants-1989_02
Patent number
US04806649

Reaction notes

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