Potassium Carbonate → 1H-1-Benzazepine
Reaction equation
CO[C:3]1[C:18](OC)=[CH:17][C:6]2[CH2:7][C:8](=O)[N:9](CCCI)[CH:10]=[CH:11][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[K+].[K+]>O>[NH:9]1[C:10]2[CH:11]=[CH:5][CH:4]=[CH:3][C:18]=2[CH:17]=[CH:6][CH:7]=[CH:8]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 52.5 °C
Procedure
7,8-Dimethoxy-3-[3-iodopropyl]-1,3-dihydro-2H-3-benzazepin-2-one (38 g) and potassium carbonate (60 g) were added to a mixture of (S)—N-[(4,5-dimethoxybenzocyclobut-1-yl)-methyl]-N-(methyl)amine (20 g) and demineralized water (100 ml) at room temperature. The reaction mixture was heated and stirred at 50-55° C. for 12-16 hours. After completion of reaction, reaction mass was cooled to 25-30° C. and the product is extracted in ethyl acetate (100 ml). The aqueous layer was further extracted with ethyl acetate (60 ml). Combined ethyl acetate layers was acidified with aqueous hydrochloric acid and stirred. The layers were separated and pH of the aqueous layer was adjusted to 10.5-12.5 with aqueous sodium hydroxide solution. The aqueous layer is extracted with ethyl acetate (140 ml+60 ml). Ethyl acetate was distilled out completely under vacuum to get the title compound.
Workup
- temperatureThe reaction mixture was heated
- customAfter completion of reaction, reaction mass
- temperaturewas cooled to 25-30° C.
- extractionthe product is extracted in ethyl acetate (100 ml)
- extractionThe aqueous layer was further extracted with ethyl acetate (60 ml)
- stirringstirred
- customThe layers were separated
- extractionThe aqueous layer is extracted with ethyl acetate (140 ml+60 ml)
- distillationEthyl acetate was distilled out completely under vacuum
Sources & evidence
- ORD record
- ord-de86898c19a94af19d645d43230d23be
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08212026B2
Reaction notes
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