Triethylamine → N-(3-bromopropyl)acetoacetamide
Reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.Br.[Br:8][CH2:9][CH2:10][CH2:11][NH2:12].C(N(CC)CC)C>C1COCC1>[Br:8][CH2:9][CH2:10][CH2:11][NH:12][C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Diketene (1.22 mL, 15.7 mmol, 1.50 equiv) was added at room temperature to a stirred mixture of 3-bromopropylamine hydrobromide (2.30 g, 10.5 mmol, 1.00 equiv) and triethylamine (1.46 mL, 10.5 mmol, 1.00 equiv) in anhydrous THF (20 mL) under argon, and stirring was continued at room temperature for 1 hour. The solvent was removed and the residue was purified by flash chromatography (SiO2, MeOH—CH2Cl2 0:1 to 1:18) to afford a light yellow oil, 2.10 g (90%), which was characterized spectroscopically.
Workup
- customThe solvent was removed
- customthe residue was purified by flash chromatography (SiO2, MeOH—CH2Cl2 0:1 to 1:18)
- customto afford a light yellow oil, 2.10 g (90%), which
Sources & evidence
- ORD record
- ord-ab1d04208ba942d5ab38c7f9319c154c
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06211198B1
Reaction notes
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