Water → 5-Phenyl-1,3-dihydro-2H-azepin-2-one

HRID 1929302Notes

Reaction equation

HRID 1929302 reaction equation
C(N(CC)[C:4]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][N:5]=1)C.[OH2:19]>COCCO>[C:11]1([C:8]2[CH:7]=[CH:6][NH:5][C:4](=[O:19])[CH2:10][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 962WaterHCID 12502457HCID 12502457, compound

Product 1

HCID 573498745-Phenyl-1,3-dihydro-2H-azepin-2-one

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

The crude diethyl-(5-phenyl-3H-azepin-2-yl)-amine (12.47 g) is added to water (10.0 mL) and 2-methoxy-ethanol (40.0 mL) and the resulting mixture heated to reflux and stirred 4½ days. The volatiles are removed in vacuo and the residue diluted with dichloromethane and washed with 0.1N HCl (2×200 mL) and saturated aqueous NaHCO3 (2×200 mL). The organic layer is dried over Na2SO4 and concentrated in vacuo to give the crude title compound as a dark brown solid (9.63 g). This material is carried into the next reaction without further purification.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureto reflux
  3. customThe volatiles are removed in vacuo
  4. additionthe residue diluted with dichloromethane
  5. washwashed with 0.1N HCl (2×200 mL) and saturated aqueous NaHCO3 (2×200 mL)
  6. dry with materialThe organic layer is dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50907c63078445fbb22162bf191b09f2
Source dataset
uspto-grants-2012_05
Patent number
US08188069B2

Reaction notes

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