Propanal → 7-[4-(2-Butoxyethoxy)phenyl]-1-propyl-2,3-dihydro-1-benzazepine-4-carboxylic acid

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Reaction Steps

To a solution of methyl 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1.0 g, 2.53 mmol) and propionaldehyde (1 ml, 13.86 mmol) in 1,2-dichloroethane (30 ml) was added sodium triacetoxyborohydride (1.9 g, 8.96 mmol) at room temperature, and the mixture was stirred for 24 hours. To the reaction system was added 1N sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate. After concentration under reduced pressure, the residue was dissolved in THF (50 ml) and methanol (50 ml), and to the solution was added 1N sodium hydroxide solution. After heating to reflux for 1 hour, the mixture was concentrated under reduced pressure. To the residue was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate. After concentration under reduced pressure, the resulting crystals were collected by filtration to give 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.895 g) as yellow crystals.

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