Ammonia → 3-(4'-Fluoro-4-biphenylyl)butylamine, hydrochloride

Participants

Reaction Steps

A solution of 27.1 g of 4-(4'-fluoro-4-biphenylyl)-pentanoic acid amide [obtainable by reacting 4-fluorobiphenyl with succinic anhydride/AlCl3 to give 4-(4'-fluoro-4-biphenylyl)-4-oxobutanoic acid, reaction with CH3MgI to give 4-(4'-fluoro-4-biphenylyl)-4-hydroxy-pentanoic acid, dehydroxylation with HI/acetic acid to give 4-(4'-fluoro-4-biphenylyl)-pentanoic acid, conversion into the chloride employing SOCl2 and reaction with NH3 ] in 150 ml of dioxane is added dropwise at 0° to a solution of 24 g of bromine in 120 ml of 20% potassium hydroxide solution. The mixture is stirred for a further 1 hour, taken up in ether, the phases are separated and the organic phase is dried over sodium sulfate and evaporated. The crude product obtained is boiled for 20 hours with 60 g of KOH, 250 ml of methanol and 65 ml of water, in the course of which 3-(4' -fluoro-4-biphenylyl)-butyl-isocyanate, which is not isolated, is formed. After cooling, the mixture is worked up using water and ether to give 3-(4'-fluoro-4-biphenylyl)-butylamine, hydrochloride; m.p. 222°-224°.

Provenance & Evidence