Diisopropylamine → Ammonia

Participants

Reaction Steps

In an atmosphere of argon, a hexane solution of n-butyl lithium (1.71M, 6.1 ml, 10.5 mmol) was added at -78° C. to a THF (10 ml) solution of diisopropylamine (1.54 ml, 11 mmol), and the mixture was stirred for 40 minutes. To the resulting solution of lithium diisopropylamide was added a THF (8 ml) solution of 2-acetylphenothiazine (1.21 g, 5.0 mmol). The mixture was stirred for 30 minutes, a THF (3 ml) solution of 3-quinuclidinone (626 mg, 5.0 mmol) was added, and the mixture was stirred for 30 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=0.8:8:92 then 2:20:80), to give the title compound (127 mg, 0.35 mmol, 7%) as yellow foam.

Provenance & Evidence