Acetyl chloride → HCID 14349089, compound

Participants

Reaction Steps

To a solution of 7,8-dimethoxy-1-(4-fluorophenoxy)-2,3,4,5-tetrahydro-3-benzazepine of Example 42, (4.3 g, 13.5 mmole) in 100 ml dichloromethane containing sodium bicarbonate (2.3 g, 27 mmole) was slowly added a solution of acetyl chloride (1.2 g, 15.6 mmole) in 25 ml dichloromethane. After stirring three hours at ambient temperature the reaction mixture was evaporated, stirred with water and extracted with ethyl acetate-ether. The organic extract was washed with diluted HCl, water, saturated NaCl and was dried (anhydrous MgSO4), filtered and evaporated to 4.2 g (89%) of an oil. A solution of the resultant 3-acetyl-7,8-dimethoxy-1-(4-fluorophenoxy)-2,3,4,5-tetrahydro-3-benzazepine (4.2 g, 11.7 mmole) in 50 ml tetrahydrofuran was slowly added to a solution of lithium aluminum hydride (1M in THF, 23 mmole, 23 ml). After stirring one hour at ambient temperature the reaction mixture was diluted with anhydrous ether and quenched by slow addition of saturated ammonium chloride. The organic phase was washed with water and saturated NaCl and was dried (anhydrous MgSO4), filtered and evaporated to 4 g of an oil. This oil was converted to the oxalate salt as in Example 1 and was recrystallized from isopropanol-ether to give 2.5 g (49%) of 7,8-dimethoxy-3-ethyl-1-(4-fluorophenoxy)-2,3,4,5-tetrahydro-3-benzazepine oxalate, d 165°-166° C.

Provenance & Evidence