Triethylamine → Nicainoprol

Participants

Reaction Steps

40 g of 1-nicotinoyl-8-hydroxy-1,2,3,4-tetrahydroquinoline ##STR9## are dissolved in 300 ml of dimethylformamide and 21 g of potassium tert.-butylate are then added at 5° C., while stirring. The mixture is stirred at 5° C. for 20 minutes, 66 g of epichlorohydrin are then added dropwise at this temperature, while stirring, and the mixture is then allowed to warm to room temperature and is subsequently stirred for 20 hours. Thereafter, the mixture is concentrated under a waterpump vacuum. The oil which remains is dissolved in water/toluene; the toluene phase is separated off, washed twice with dilute aqueous sodium hydroxide solution and once with water, dried and concentrated under a waterpump vacuum. A solid residue, which can be reacted directly with isopropylamine to give 1-nicotinoyl-8-[(3-isopropylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydroquinoline, remains. The 1-nicotinoyl-8-hydroxy-1,2,3,4-tetrahydroquinoline used as the starting material is obtained in the customary manner by reacting 8-hydroxy-1,2,3,4-tetrahydroquinoline with nicotinic acid chloride hydrochloride in toluene at room temperature in the presence of triethylamine. (Melting point: 122° C.).

Provenance & Evidence