6H-DIBENZ[B,D]AZEPIN-6-ONE, 5,7-DIHYDRO-5-METHYL-

6H-DIBENZ[B,D]AZEPIN-6-ONE, 5,7-DIHYDRO-5-METHYL- Property

Melting point:

155-160℃

Boiling point:

474.1±24.0 °C(Predicted)

Density 

1.166

storage temp. 

Sealed in dry,Room Temperature

solubility 

Dichloromethane, Methanol

form 

Solid

pka

0.49±0.20(Predicted)

color 

Off-White to Pale Yellow

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

6H-DIBENZ[B,D]AZEPIN-6-ONE, 5,7-DIHYDRO-5-METHYL- Chemical Properties,Usage,Production

Chemical Properties

White Solid

Uses

An intermediate in the production of γ-secretase inhibitors.

Synthesis

Step A - Synthesis of 7-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one: Sodium hydride (0.295 g, 7.46 mmol) and 9.0 mL of anhydrous DMF were added to a dry round-bottomed flask, and stirred until completely dissolved. Subsequently, 5,7-dihydro-6H-dibenzo[b,d]azepin-6-one (1.3 g, 6.22 mmol) was added, and the reaction mixture was stirred at 60 °C for 1 hour. Then, iodomethane (1.16 mL, 18.6 mmol) was slowly added dropwise and stirring was continued for 17 h under light protection. After completion of the reaction, the mixture was cooled to room temperature, diluted with a mixture of dichloromethane and water, washed sequentially with NaHSO4 solution and water, and the organic phase was dried with anhydrous Na2SO4. After concentration under reduced pressure, it was purified by fast column chromatography (silica gel, chloroform as eluent) to afford 0.885 g (63% yield) of the target compound, 5-methyl-5H-dibenz[b,d]azepin-6(7H)-one, as a colorless solid. Nuclear Magnetic Resonance Hydrogen Spectroscopy (1H-NMR, CDCl3) data: δ= 7.62 (d, 2H), 7.26-7.47 (m, 6H), 3.51 (m, 2H), 3.32 (s, 3H). Elemental analysis: C15H13NO (molecular weight = 223.27); mass spectrum (MH+) 223. calculated values: C, 80.69; H, 5.87; N, 6.27. measured values: C, 80.11; H, 5.95; N, 6.23.

References

[1] Organic Letters, 2008, vol. 10, # 21, p. 4871 - 4874
[2] Journal of Organic Chemistry, 2010, vol. 75, # 17, p. 5984 - 5993
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6392 - 6395
[4] Patent: EP951466, 2009, B1. Location in patent: Page/Page column 72
[5] Patent: US6958330, 2005, B1. Location in patent: Page/Page column 38-39