Tetrahydrofuran → HCID 19799613, compound

Participants

Reaction Steps

A solution of 2.8 g (0.01 mole) of 3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride in 20 ml of tetrahydrofuran was stirred with 1.4 g (0.01 mole) of potassium carbonate then treated with the dropwise addition of 1.3 g (0.01 mole) of 1,4-diazabicyclo(4.3.0)nonane. After stirring for 30 minutes, approximately 2 g of ice was added and stirring continued for 64 hr. The reaction mixture was diluted with 200 ml of water and the oil which separated was extracted into methylene chloride (2×50 ml), dried over magnesium sulfate and concentrated in vacuo to a pale yellow oil (3.9 g). This oil was placed in 25 ml of isopropanol and treated with 1.2 g of fumaric acid and heated to give a clear solution. The solvent was removed in vacuo and the residue crystallized on standing. The residue was recrystallized from ethyl acetate with 5% isopropyl ether and from methyl isobutyl ketone to yield 2.5 g (51.5%) of beige colored crystals, m.p. 102°-110° C.

Provenance & Evidence