Triethylamine → 3-(2-Fluorobenzoyl)amino-epsilon-caprolactam

HRID 1463468Notes

Reaction equation

HRID 1463468 reaction equation
[NH2:1][CH:2]1[CH2:9][CH2:8][CH2:7][NH:6][C:4](=[O:5])[CH2:3]1.C(N(CC)CC)C.[F:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>C(Cl)Cl>[F:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:1][CH:2]1[CH2:9][CH2:8][CH2:7][NH:6][C:4](=[O:5])[CH2:3]1)=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98082-Fluorobenzoyl chlorideHCID 215841384-Aminoazepan-2-one

Product 1

HCID 190904013-(2-Fluorobenzoyl)amino-epsilon-caprolactam

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Amino-ε-caprolactam (11.0 g) and triethylamine (15.7 ml) were added to 200 ml of methylenechloride. Then a solution of 2-fluorobenzoyl chloride (15.0 g) in methylenechloride (30 ml) was added dropwise to the mixture under ice-cooling and stirring. Thereafter, the mixture was stirred for 1.5 hrs. at room temperature, and the resultant precipitate was collected by filtration to give 3-(2-fluorobenzoyl)amino-ε-caprolactam as crude crystals. This crystals and phosphorus pentasulfide (16.5 g) were added to 200 ml of pyridine, and the whole was refluxed for 12 hrs. After cooling, the pyridine was removed by distillation, and to the residue was added a saturated sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with water, dried, and the solvent was distilled off under reduced pressure. The residue was purified by a column chromatography on silica gel, and then recrystallized from ethyl ether to give the title compound (4.55 g, 24.7%).

Workup

  1. temperaturecooling
  2. stirringThereafter, the mixture was stirred for 1.5 hrs
  3. filtrationat room temperature, and the resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-9f8a579b6843469f91f986204b7f4374
Source dataset
uspto-grants-1994_04
Patent number
US05300639

Reaction notes

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