Sodium Hydroxide → HCID 24956502, compound

Participants

Reaction Steps

(±)-Dimethyl-[1-phenyl-4-(3-pyridin-2-ylmethyl-1H-indol-2-yl)cyclohex-3-enyl]amine Trifluoromethanesulfonic acid (3.95 g, 2.30 ml, 26 mmol) was added to a solution of Ind-49 (2.17 g 10.4 mmol) and Ket-10 (2.70 g, 12.5 mmol) in anhydrous methylene chloride (80 ml), while cooling with ice. The reaction mixture was stirred at room temperature for 2 d and 0.5 M sodium hydroxide solution (50 ml) was then added and the mixture was stirred at room temperature for 2 h. The phases were separated, the aqueous phase was extracted with methylene chloride (3×30 ml) and the combined organic phases were dried with sodium sulfate and concentrated i. vac. The crude product (6.45 g) was purified by flash chromatography (400 g, 20×7.6 cm) with chloroform/methanol (9:1).

Provenance & Evidence