5,5-Dibromobarbituric acid → Tert-butyl 4-(2-bromo-3-oxopropyl)piperidine-1-carboxylate

HRID 493715Notes

Reaction equation

HRID 493715 reaction equation
[O:1]=[CH:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[Br:18]C1(Br)C(=O)NC(=O)NC1=O>C(OCC)C>[Br:18][CH:3]([CH:2]=[O:1])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 948775,5-Dibromobarbituric acidHCID 10657745Tert-butyl 4-(3-oxopropyl)piperidine-1-carboxylate

Product 1

HCID 23131015Tert-butyl 4-(2-bromo-3-oxopropyl)piperidine-1-carboxylateYield 167%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of tert-butyl 4-(3-oxopropyl)piperidine-1-carboxylate (Wityak J., et al., J. Med. Chem., 40, p. 50 (1997): 27.6 g) in diethyl ether was added dibromobarbituric acid (17.0 g), and the mixture was mixed for 12 hours. The insolubles were filtered off, and the filtrate was diluted with diethyl ether, sequentially washed with a saturated aqueous sodium bicarbonate solution and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off to give the title compound (31.8 g) as a pale yellow viscous oily matter.

Workup

  1. additionthe mixture was mixed for 12 hours
  2. filtrationThe insolubles were filtered off
  3. additionthe filtrate was diluted with diethyl ether
  4. washsequentially washed with a saturated aqueous sodium bicarbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-5852e06dda4b4208955b6388ca012799
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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