Triethylamine → alpha-N-(4-Nitrophenyl)amino-epsilon-caprolactam

HRID 986876Notes

Reaction equation

HRID 986876 reaction equation
[NH2:1][CH:2]1[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:3]1=[O:4].C(N(CC)CC)C.F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>CN(C)C=O>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([NH:1][CH:2]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:3]2=[O:4])=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9590p-FluoronitrobenzeneHCID 1024632H-Azepin-2-one, 3-aminohexahydro-

Product 1

HCID 70002500alpha-N-(4-Nitrophenyl)amino-epsilon-caprolactamYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g (39 mmol) of α-amino-ε-caprolactam are dissolved in 50 ml of dimethylformamide and 5.5 ml (1 eq) of triethylamine in a 100 ml three-necked flask equipped with a reflux condenser and a thermometer. 4.1 ml (1.5 eq) of 4-fluoronitrobenzene are then run into the reaction mixture, which is subsequently brought to a temperature of 70° C. for 48 hours. The mixture is cooled and is then precipitated from water. An orangy-yellow precipitate is isolated by filtration and is then purified on a silica column (eluent: dichloromethane 95/methanol 5). 2.7 g of a yellow product are obtained, i.e. a final yield of 28%.

Workup

  1. temperatureThe mixture is cooled
  2. customis then precipitated from water
  3. customAn orangy-yellow precipitate is isolated by filtration
  4. customis then purified on a silica column (eluent: dichloromethane 95/methanol 5)

Sources & evidence

ORD record
ord-0f6ff56efcd646e8b120072c727f1b2a
Source dataset
uspto-grants-2003_10
Patent number
US06630004B1

Reaction notes

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