Ethanolamine → HCID 18914376, compound

Participants

Reaction Steps

(2-Methyl-quinolin-2-yl)-[2-(2-methyl-quinolin-4-yloxy)-ethyl]amine ##STR56## 0.72 g (2.9 mmol) of 4-(2-hydroxyethyl)amino-2-methylquinoline hydrochloride, obtained from 4-chloroquinaldine and ethanolamine, in 20 ml of absolute DMF are treated with 100 mg (3.2 mmol) of 80% pure sodium hydride in paraffin under argon. After the mixture has been stirred for 1 hour at 50° , a further 0.3 g of 4-chloroquinaldine is added. After the mixture has been stirred for 20 hours at 50°, a further 100 mg of sodium hydride, as above, are added, and the mixture is stirred for a further 18 hours. The reaction batch is concentrated. Flash chromatography (silica gel K60; methylene chloride, then methylene chloride/ethanol/ammonia 100:10:1) gives a crude product which is purified by recrystallization from isopropanol. This gives 122 mg (22%) of colorless crystals, m.p. 247°-248° C.

Provenance & Evidence