Hydrogen Bromide → 3-Bromopiperidin-4-one hydrobromide

HRID 400425Notes

Reaction equation

HRID 400425 reaction equation
[BrH:1].BrBr.[NH:4]1[CH2:9][CH2:8][C:7]([OH:11])(O)[CH2:6][CH2:5]1>C(O)(=O)C>[BrH:1].[Br:1][CH:6]1[C:7](=[O:11])[CH2:8][CH2:9][NH:4][CH2:5]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 3853601Piperidine-4,4-diol

Product 1

HCID 141969683-Bromopiperidin-4-one hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

4.7 mL 33% HBr in acetic acid, 11.4 g bromine in 30 mL acetic acid was added slowly to a stirred solution of 10 g piperidine-4,4-diol in 60 mL acetic acid at RT. The reaction mixture was stirred 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 hour, cooled, filtered and washed with acetone and dried to give 15.2 g of the desired product

Workup

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

Sources & evidence

ORD record
ord-af3b2156280f449c9baed7510c77a423
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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