10-(β-Hydroxypropyl)phenothiazine synthesis

Yield:-

Reaction Conditions:

with methyloxirane in 5,5-dimethyl-1,3-cyclohexadiene;water

Steps:

12 Synthesis of 10-(2-hydroxypropyl)phenothiazine (1)
EXAMPLE 12 Synthesis of 10-(2-hydroxypropyl)phenothiazine (1) A solution of phenothiazine (5 g, 25.1 mmol) and sodium amide (95%, 1.2 g, 29 mmol) in xylene (30 ml) was heated under reflux for 3 hours. Then propylene oxide (2.5 ml, 37 mmol) was added thereto under ice-cooling, and the reaction mixture was heated under reflux for 3 hours. To the reaction mixture was added water, and the mixture was extracted with chloroform, washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated. The thus-obtained black-brown solution containing xylene was purified by column chromatography on silica gel to give a dark black oil. Yield 4.19 g (65%).

References:

Green Cross Corporation US5308840, 1994, A