1,3-Dibromopropane → 4-(3-Bromo-propyl)-morpholine-3,5-dione

HRID 1929015Notes

Reaction equation

HRID 1929015 reaction equation
[NH:1]1[C:6](=[O:7])[CH2:5][O:4][CH2:3][C:2]1=[O:8].[Br:9][CH2:10][CH2:11][CH2:12]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:9][CH2:10][CH2:11][CH2:12][N:1]1[C:6](=[O:7])[CH2:5][O:4][CH2:3][C:2]1=[O:8]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 364836Morpholine-3,5-dione

Product 1

HCID 596001324-(3-Bromo-propyl)-morpholine-3,5-dione

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A pale yellow suspension of morpholine-3,5-dione (1.2 g, 10 mmol), of 1,3-dibromopropane (3.4 ml, 33 mmol), and potassium carbonate (2.7 g, 19 mmol) in 23 ml of 2-butanone is refluxed under an argon atmosphere for 22 hours. After cooling, the suspension is concentrated on a rotary evaporator, poured into ice/water, and extracted twice with ethyl acetate. The combined organic phases are washed with brine, dried over anhydrous sodium sulphate, and evaporated. The residual yellow oil (2.06 g) is purified by chromatography (Biotage 40 Mi, I=15 cm, cyclohexane/ethyl acetate 3:1).

Workup

  1. temperatureAfter cooling
  2. concentrationthe suspension is concentrated on a rotary evaporator
  3. additionpoured into ice/water
  4. extractionextracted twice with ethyl acetate
  5. washThe combined organic phases are washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. customevaporated
  8. customThe residual yellow oil (2.06 g) is purified by chromatography (Biotage 40 Mi, I=15 cm, cyclohexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-6e486bd785d54325b3a97187f2d04817
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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