A solution of 3.9 g. (16 mmole) 3-(1,1-dimethyl-3-phenylpropylamino)-1,2-dihydroxypropane, 15 ml. benzaldehyde, 9 ml. benzene, and 100 mg. benzoic acid was refluxed for 16 hours while a Dean-Stark trap was being used to collect the water. The solution was diluted with benzene and washed with aqueous potassium carbonate. The mixture was concentrated and the residue was distilled under reduced pressure (0.4 mm.) at a pot temperature of 75°-80° C. The residue from above in 50 ml DMF was then added dropwise to sodium hydride (1.0 g. of a 50% oil dispersion washed with hexane) in 25 ml. DMF. After the addition, stirring was continued for 1 hour. 2-Chloropyridine (1.80 g., 16 mmole) in 25 ml. DMF was added and the mixture heated at 70° C. for 16 hours. Most of the DMF was evaporated. Water and ether were added and the layers separated. The ether solution was washed twice with 100 ml. 4N HCl and the combined acid washings were heated on a steam bath for 1/2 hour. After washing with ether, the aqueous phase was made basic with KOH. The oil was extracted with CH2Cl2, dried (NA2SO4), and concentrated to give 3.0 g. (60%) of the crude free base. A small sample was used to prepare the maleate salt in 2-propanol/ether, and recrystallization of this from 2-propanol gave pure 2-[3-(1,1-dimethyl-3-phenylpropylamino)-2-hydroxy-1-propoxy]pyridine maleate, mp 144°-146° C.
