Benzoyl chloride → 1-Benzoyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

HRID 220779

Reaction equation

HRID 220779 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl.C(N(CC)CC)C.CCOC(C)=O>[C:13]([N:1]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 7412Benzoyl chlorideHCID 2947881,2,3,4-Tetrahydro-benzo(b)azepin-5-one

Product 1

HCID 231123881-Benzoyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-oneYield 56%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,2,3,4-Tetrahydro-benzo[b]azepin-5-one from Example E5.5 (480 mg, 2.98 mmol) was dissolved in a mixture of dichloromethane (30 ml) and triethylamine (1.3 ml). Benzoyl chloride (0.46 g, 3.28 mmol) was added and the reaction mixture was heated for at reflux for 2 h. The mixture was cooled and reduced in vacuo. The residue was dissolved in EtOAc and washed with 1M KHSO4 (aq), water and brine. The organic layer was dried, filtered and reduced in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 50% EtOAc: 50% hexane) to yield the title compound (440 mg, 56%).

Workup

  1. temperaturethe reaction mixture was heated for
  2. temperatureat reflux for 2 h
  3. temperatureThe mixture was cooled
  4. washwashed with 1M KHSO4 (aq), water and brine
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customThe residue was purified by flash chromatography on silica gel (eluant; 50% EtOAc: 50% hexane)

Sources & evidence

ORD record
ord-e009fb4c82ad4e8794c0ab9b295570ea
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Linked notes

Loading…