Dichloromethane → 5-amino-7-(methoxyacetyl)-5,7-dihydro-6H-dibenz[b,d]azepin-6-one hydrochloride

HRID 433400Notes

Reaction equation

HRID 433400 reaction equation
C([NH:8][N:9]1[C:15](=[O:16])[CH2:14][C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[C:11]2[CH:21]=[CH:22][CH:23]=[CH:24][C:10]1=2)(OC(C)(C)C)=O.[C:25]([O-:28])([O-])=O.[Cs+].[Cs+].[C:31]([O:34][CH2:35]Br)(=O)C.C(Cl)[Cl:38]>CN(C=O)C>[ClH:38].[NH2:8][N:9]1[C:15](=[O:16])[CH:14]([C:25](=[O:28])[CH2:31][O:34][CH3:35])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[C:11]2[CH:21]=[CH:22][CH:23]=[CH:24][C:10]1=2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 68536Bromomethyl acetateHCID 114935485-(N-Boc-amino)-5,7-dihydro-6H-dibez[b,d]azepin-6-one

Product 1

HCID 223126355-amino-7-(methoxyacetyl)-5,7-dihydro-6H-dibenz[b,d]azepin-6-one hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5-(N-Boc-amino)-5,7-dihydro-6H-dibenz[b,d]azepin-6-one (1.03, 3.08 mmol) (Example 7-E) in DMF was treated with Cs2CO3 (1.10 g, 3.39 mmol) and warmed to 60° C. To the reaction mixture was added bromomethyl acetate (0.321 ml, 3.39 mmol) (Aldrich) and stirring continued for 17 h. After cooling to 23° C. the mixture was diluted with CH2Cl2, washed with several portions of brine and dried over Na2SO4. The title compound was purified by chromatography (SiO2, CHCl3).

Workup

  1. temperatureAfter cooling to 23° C. the mixture
  2. washwashed with several portions of brine
  3. dry with materialdried over Na2SO4
  4. customThe title compound was purified by chromatography (SiO2, CHCl3)

Sources & evidence

ORD record
ord-4907de89fa464c73ae11c38022e8170f
Source dataset
uspto-grants-2003_12
Patent number
US06667305B1

Reaction notes

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