trans-1,4-Dibromo-2-butene → Ammonia
Reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1)[CH3:2].Br[CH2:10]/[CH:11]=[CH:12]/[CH2:13]Br>C(#N)C>[CH2:1]([N:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH2:10]/[CH:11]=[CH:12]/[CH2:13][N:5]2[CH2:6][CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4]2)[CH2:4]1)[CH3:2].[NH3:3]Participants
Reactant 2
Product 2
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 1.07 g (9.37 mmol) of 1-ethyl-hexahydro-pyrimidine (Chem. Pharm. Bull. 28, 3310 (1980)), 0.5 g (2.34 mmol) of trans-1,4-dibromo-2-butene and 10 ml of acetonitrile is heated for 16 h at 80° C., with stirring and under a nitrogen atmosphere, and is then concentrated by evaporation in vacuo. The residue is partitioned between 2N sodium hydroxide solution and methylene chloride, and the methylene chloride phase is washed with brine, dried over sodium sulfate and concentrated by evaporation in vacuo. The residue is purified by means of flash chromatography over silica gel having a particle size of 0.04-0.063 mm, using methylene chloride-methanol (9:1) and methylene chloridemethanol-concentrated ammonia (90:10:0.5), yielding the title compound in the form of an oil, Rf value=0.63 (silica gel/methylene chloride:methanol:concentrated ammonia (40:10:1)).
Workup
- concentrationis then concentrated by evaporation in vacuo
- customThe residue is partitioned between 2N sodium hydroxide solution and methylene chloride
- washthe methylene chloride phase is washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated by evaporation in vacuo
- customThe residue is purified by means of flash chromatography over silica gel having a particle size of 0.04-0.063 mm
Sources & evidence
- ORD record
- ord-159bb39509ff439986aa7f9de8ecc7b7
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05627215
Reaction notes
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