Dichloromethane → 3-Bromopiperidine-2,4-dione

HRID 220371Notes

Reaction equation

HRID 220371 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][C:2]1=[O:8].[Br:9]Br.ClCCl>C(O)(=O)C>[Br:9][CH:3]1[C:4](=[O:7])[CH2:5][CH2:6][NH:1][C:2]1=[O:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24408BromineHCID 108878632,4-Piperidinedione

Product 1

HCID 581805393-Bromopiperidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of piperidine-2,4-dione (0.072 g, 0.637 mmol) in acetic acid (1.591 mL) was added bromine (0.033 mL, 0.637 mmol) dropwise. The reaction mixture was stirred at rt 70 min. Dichloromethane was added and the cloudy mixture was concentrated in vacuo. The residual solution was treated with ethyl ether. A white solid crashed out and the AcOH/ether was decanted. The white solid, presumed to be product was carried forward. The white solid started liquifying and turning red rapidly upon exposure to light and standing.

Workup

  1. concentrationthe cloudy mixture was concentrated in vacuo
  2. additionThe residual solution was treated with ethyl ether
  3. customwas decanted

Sources & evidence

ORD record
ord-5544b90978e64c21aad8725ada788375
Source dataset
uspto-grants-2012_06
Patent number
US08202881B2

Reaction notes

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