Triethylamine → N-(3-bromopropyl)acetoacetamide

HRID 382683Notes

Reaction equation

HRID 382683 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-66c4b32fe6ae41f9948be1219d3d38d5
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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