Triethylamine → N-(3-bromopropyl)acetoacetamide

HRID 396626Notes

Reaction equation

HRID 396626 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

HCID 8471TriethylamineHCID 12661DiketeneHCID 787013-Bromopropylamine hydrobromide

Product 1

HCID 23004079N-(3-bromopropyl)acetoacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customThe solvent was removed
  2. customthe residue was purified by flash chromatography (SiO2, MeOH-CH2Cl2 0:1 to 1:18)
  3. customto afford a light yellow oil, 2.10 g (90%), which

Sources & evidence

ORD record
ord-28fcd7511ee449f785a664f8efc8b35c
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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