Water → HCID 21072524, compound

HRID 1374566Notes

Reaction equation

HRID 1374566 reaction equation
[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][C:7](=[O:16])[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:6]2[C:7](=[O:16])[CH2:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 113677988-Azatricyclo[9.4.0.0,2,7]pentadeca-1(15),2,4,6,11,13-hexaen-9-one

Product 1

HCID 21072524HCID 21072524, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.82 g (4 mmol) of 5H,7H-dibenzo[b,d]azepin-6-one in 15 ml of dimethylformamide at room temperature 0.20 g (5 mmol) of sodium hydride 55% in oil was added. After stirring for 30 min at room temperature 0.75 g (5 mmol) of p-methoxybenzyl chloride were added and stirring was continued at room temperature for 2 hours. For workup the mixture was distributed between water and ethyl acetate. The organic layer was re-extracted with 1 N hydrochloric acid and the aqueous layers were washed with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (hexane/ethyl acetate=1:1) to yield 1.175 g (91%) of 5-(4-methoxybenzyl)-5H,7H-dibenzo[b,d]azepin-6-one as a colourless oil; MS: m/e: 330.4 (M+H+).

Workup

  1. additionwere added
  2. extractionThe organic layer was re-extracted with 1 N hydrochloric acid
  3. washthe aqueous layers were washed with ethyl acetate
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-89f7947dc3a64d2a8f8b9470a7df7b27
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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