Bromine → 1-(1-Acetylpiperidin-4-yl)-2-bromoethan-1-one

HRID 911085Notes

Reaction equation

HRID 911085 reaction equation
[N:1]1([C:10](=[O:12])[CH3:11])[CH2:6][CH2:5][CH:4]([C:7](=[O:9])[CH3:8])[CH2:3][CH2:2]1.[Br:13]Br>CO>[C:10]([N:1]1[CH2:6][CH2:5][CH:4]([C:7](=[O:9])[CH2:8][Br:13])[CH2:3][CH2:2]1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 27772501,4-Diacetylpiperidine

Product 1

HCID 772303261-(1-Acetylpiperidin-4-yl)-2-bromoethan-1-oneYield 80.23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,1′-(Piperidine-1,4-diyl)diethanone (38.00 g, 224.6 mmol) was dissolved in methanol (700 ml) and bromine (12.11 ml, 235.8 mmol) was added in portions. The resulting mixture was agitated 3 hours and the solvent was removed in vacuo. The resulting solid was triturated with ethyl acetate and partitioned between ethyl acetate and sodium carbonate solution. The organic phase was separated, washed with brine, dried and evaporated to give the desired product (44.70 g, 80.23% yield) as yellow solid.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe resulting solid was triturated with ethyl acetate
  3. custompartitioned between ethyl acetate and sodium carbonate solution
  4. customThe organic phase was separated
  5. washwashed with brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-af048f9ba91947b9ae486612e35e08d6
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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