Water → 1-Acetyl-4-(2,5-difluorobenzoyl)-4-bromopiperidine

HRID 3967Notes

Reaction equation

HRID 3967 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=[O:19])[C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[F:18])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Br:20]Br.O>C(O)(=O)C.C(OCC)(=O)C>[C:1]([N:4]1[CH2:9][CH2:8][C:7]([C:10](=[O:19])[C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[F:18])([Br:20])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 138001311-Acetyl-4-(2,5-difluorobenzoyl)piperidine

Product 1

HCID 138001321-Acetyl-4-(2,5-difluorobenzoyl)-4-bromopiperidine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 11.2 g of 1-acetyl-4-(2,5-difluorobenzoyl)piperidine in 225 ml of glacial acetic acid was added dropwise over 0.5 hr a solution of 13.5 ml (42.1 g) of bromine in 115 ml of glacial acetic acid at a rate such that the temperature remained between 10°-12° C. The mixture was stirred for an additional 10-15 mins, poured into water, extracted twice with ethyl acetate, and the solvent evaporated to provide an oil. The oil was dissolved in ethyl acetate, washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered, and the solvent evaporated to provide product as an oil.

Workup

  1. customremained between 10°-12° C
  2. extractionextracted twice with ethyl acetate
  3. customthe solvent evaporated
  4. customto provide an oil
  5. washwashed with saturated sodium bicarbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customto provide product as an oil

Sources & evidence

ORD record
ord-2caa6a90f66045989bb3fe05bb837dcc
Source dataset
uspto-grants-1988_02
Patent number
US04723009

Reaction notes

Loading…