Diisopropylamine → HCID 53760246, compound

Participants

Reaction Steps

In an atmosphere of argon, a hexane solution of n-butyl lithium (1.71M, 4.94 ml, 8.45 mmol) was added at -78° C. to a THF (8 ml) solution of diisopropylamine (1.23 ml, 8.8 mmol), and the mixture was stirred for 40 minutes. To the solution of the resulting lithium diisopropylamide was added a THF (8 ml) solution of 2-acetyl-10-methylphenothiazine (1.96 g, 7.68 mmol), and the mixture was stirred for 1 hour. A THF (8 ml) solution of 3-quinuclidinone (951 mg, 7.60 mmol) was added, the mixture was stirred at -78° C. for 30 minutes and then with ice-cooling for 15 minutes. Water was added to the reaction mixture and the reaction product was extracted with chloroform. The extract was washed with saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; 29% aqueous ammonia:methanol:chloroform=1:10:90) to give the title compound (1.55 g, 4.07 mmol, 53%) as yellow foam.

Provenance & Evidence