Triethylamine → N-(3-bromopropyl)acetoacetamide

HRID 322130

Reaction equation

HRID 322130 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-ab1d04208ba942d5ab38c7f9319c154c
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Linked notes

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