Hydrogen Bromide → N-benzyl-5-bromohexahydro-4-azepinone

HRID 239170Notes

Reaction equation

HRID 239170 reaction equation
[BrH:1].BrBr.[CH2:4]([N:11]1[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)(=O)C>[CH2:4]([N:11]1[CH2:17][CH2:16][CH:15]([Br:1])[C:14](=[O:18])[CH2:13][CH2:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 15143501-Benzyl-hexahydro-4H-azepin-4-one

Product 1

HCID 20803026N-benzyl-5-bromohexahydro-4-azepinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

33% hydrobromic acid in conc. acetic acid and 1.97 g bromine was added to 5 g 1-benzyl-azepane-4-one in 15 mL conc. acetic acid. The reaction was stirred 2 h at RT and completely concentrated under reduced pressure. The residue was diluted with ethyl acetate and refluxed for 1 h and crystallized with ethyl acetate to give 4 g of the desired product.

Workup

  1. concentrationcompletely concentrated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. temperaturerefluxed for 1 h
  4. customcrystallized with ethyl acetate

Sources & evidence

ORD record
ord-ad912c6a02b543b3b5f7f29869c07493
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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