Hydrogen Bromide → 3-Bromopiperidin-4-one hydrobromide

HRID 239100Notes

Reaction equation

HRID 239100 reaction equation
[BrH:1].BrBr.[NH:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1>C(O)(=O)C>[BrH:1].[Br:1][CH:6]1[C:7](=[O:10])[CH2:8][CH2:9][NH:4][CH2:5]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 337214-Piperidone

Product 1

HCID 141969683-Bromopiperidin-4-one hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

4.7 mL 33% HBr in acetic acid and 11.4 g bromine in 30 mL acetic acid were added slowly to a stirred solution of 10 g piperidin-4-one in 60 mL acetic acid at RT. The reaction mixture was stirred for additional 45 min at ambient temperature and the acetic acid was completely removed under reduced pressure. The residue was dissolved in 200 mL acetone and refluxed for 1 h, cooled, filtered and washed with acetone and dried to give 15.2 g of the desired product, (M+H)+: 180.

Workup

  1. customthe acetic acid was completely removed under reduced pressure
  2. dissolutionThe residue was dissolved in 200 mL acetone
  3. temperaturerefluxed for 1 h
  4. temperaturecooled
  5. filtrationfiltered
  6. washwashed with acetone
  7. customdried

Sources & evidence

ORD record
ord-3576c591157a4f3b95b222bbb834b6a9
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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