Dichloromethane → 10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carbonitrile
Reaction equation
C(Cl)Cl.[C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2)#[N:5].BrN1C(=[O:27])CCC1=O>O>[C:4]([N:6]1[C:7]2[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=2[CH:9]([OH:27])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]1=2)#[N:5]Participants
Conditions
- Temperature
- 0 °C
Procedure
150 ml of CH2Cl2, 25 g of (I) and 21 g of N-bromosuccinimide are loaded under nitrogen in a 500 ml pyrex round-bottom flask, and irradiated from the outside with a 300 watt halogen lamp, refluxing for 2 hours. 150 ml of water are added. 80 ml of CH2Cl2 are distilled off, 150 ml of toluene and 5 g of PEG 6000 are added while distilling off CH2Cl2 at inner temperature of 85-90° C. The mixture is left for 3 hours at said temperature, water is removed at 60° C., the mixture is washed with 2×50 ml of water and 30-40 ml of toluene are distilled off at 40 mm/Hg. The mixture is cooled at 0° C. for 2-3 hours, filtered, washed with 20 ml of toluene at 0° C. and air-dried at 60° C., to obtain 20.4 g of (VI) m.p. 110-111° C., with good purity. From mother liquors a further 1.8 g are recovered (overall yield 82%).
Workup
- temperaturerefluxing for 2 hours
- distillation80 ml of CH2Cl2 are distilled off
- addition150 ml of toluene and 5 g of PEG 6000 are added
- distillationwhile distilling off CH2Cl2 at inner temperature of 85-90° C
- customis removed at 60° C.
- washthe mixture is washed with 2×50 ml of water and 30-40 ml of toluene
- distillationare distilled off at 40 mm/Hg
- filtrationfiltered
- washwashed with 20 ml of toluene at 0° C.
- customair-dried at 60° C.
Sources & evidence
- ORD record
- ord-eed34f582cc84bafa68e0725ae0c708f
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06384217B1
Reaction notes
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