Water → HCID 11484696, compound

HRID 346459Notes

Reaction equation

HRID 346459 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:18]=[CH:17][C:10]2[CH2:11][C:12](=[O:16])[NH:13][CH2:14][CH2:15][C:9]=2[CH:8]=1.[C:22]([O-])(=[O:24])[CH3:23].[Na+].O.ClCCl>C(OC(=O)C)(=O)C>[C:22]([N:13]1[CH2:14][CH2:15][C:9]2[CH:8]=[C:7]([O:6][CH2:5][C:4]3[CH:19]=[CH:20][CH:21]=[C:2]([Cl:1])[CH:3]=3)[CH:18]=[CH:17][C:10]=2[CH2:11][C:12]1=[O:16])(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 517045Sodium AcetateHCID 11150792HCID 11150792, compound

Product 1

HCID 11484696HCID 11484696, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 50 mg (0.2 mmol) of 7-(3-chloro-benzyloxy)-1,3,4,5-tetrahydro-benzo[d]azepin-2-one and 33 mg (0.4 mmol) of sodium acetate in 0.12 ml of acetic acid anhydride was heated to 145° C. during 4.5 hours. For the working-up, the reaction mixture was cooled and treated with water and dichloromethane. The organic layer was separated, washed with a saturated solution of sodium hydrogencarbonate, and, finally, evaporated. For purification, the crude material obtained was chromatographed on silica gel using a 4:1-mixturet of heptane and ethyl acetate as the eluent. There were obtained 45 mg (79% of theory) of 3-acetyl-7-(3-chloro-benzyloxy)-1,3,4,5-tetrahydro-benzo[d]azepin-2-one as a white foam; MS: m/e=344 (M+H)+.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customThe organic layer was separated
  3. washwashed with a saturated solution of sodium hydrogencarbonate
  4. customfinally, evaporated
  5. customFor purification
  6. customthe crude material obtained
  7. customwas chromatographed on silica gel using a 4

Sources & evidence

ORD record
ord-2d62c8646d7947dabfaae897573f0b04
Source dataset
uspto-grants-2007_02
Patent number
US07173023B2

Reaction notes

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