5,10-Dihydro-11H-dibenzo(b,e)(1,4)diazepin-11-one → 10,11-Dihydro-5h-dibenzo[b,e][1,4]diazepine

Temperature

110 °C

To a stirred solution of 4.3 g of 5,11-dihydro-10H-dibenz[b,e][1,4]diazepin-11-one in 50 ml of tetrahydrofuran, under nitrogen and cooled to 0° C. is added 4.0 ml of a 10 molar solution of dimethyl sulfide-borane complex in tetrahydrofuran. The ice bath is removed after 30 minutes and the reaction mixture stirred at room for 18 hours. The reaction mixture is cooled in an ice bath and 30 ml of anhydrous methanol added dropwise and evaporated to dryness in vacuo. Another 30 ml of methanol is added and evaporated to a residue. The residue is quenched with 30 ml of 40% sodium hydroxide followed by heating at 110° C. for 45 minutes and cooling to room temperature. The reaction mixture is diluted with 200 ml of water and extracted with methylene chloride (3×100 ml). The combined extracts are washed with 1N HCl, water and 0.5N NaOH. The organic layer is dried and evaporated in vacuo to give 3.2 g of the desired product, m.p. 114°-116° C.

1. customThe ice bath is removed after 30 minutes
2. temperatureThe reaction mixture is cooled in an ice bath
3. addition30 ml of anhydrous methanol added dropwise
4. customevaporated to dryness in vacuo
5. additionAnother 30 ml of methanol is added
6. customevaporated to a residue
7. customThe residue is quenched with 30 ml of 40% sodium hydroxide
8. temperaturecooling to room temperature
9. additionThe reaction mixture is diluted with 200 ml of water
10. extractionextracted with methylene chloride (3×100 ml)
11. washThe combined extracts are washed with 1N HCl, water and 0.5N NaOH
12. customThe organic layer is dried
13. customevaporated in vacuo

ORD record

ord-746af68681f5406c804661b58e33e079

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05849735