Hexane → HCID 18942236, compound

Participants

Reaction Conditions

Reaction Steps

In an atmosphere of argon, a hexane solution of n-butyl lithium (1.65M, 10.1 ml, 16.7 mmol) was added at -78° C. to a THF (25 ml) solution of 3-(2,2-dibromovinyl)-10-methylphenothiazine (3.13 g, 7.94 mmol), and the mixture was stirred for 1 hour and then at room temperature for 1 hour. The reaction mixture was again cooled at -78° C., and a THF (8 ml) solution of 3-quinuclidinone (1.09 g, 8.70 mmol) was added dropwise. The mixture was stirred at -78° C. for 1 hour and then with ice-cooling for 30 minutes. Water (5 ml) was added to the reaction mixture and the mixture was concentrated under a reduced pressure. A potassium carbonate aqueous solution was added and the reaction product was extracted with chloroform which was heated at about 50° C. The extract was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The resulting residue was recrystallized from ethanol-chloroform to give the title compound (1.75 g, 4.83 mmol, 61%) as yellow crystals.

Provenance & Evidence