Sodium Hydroxide → HCID 24956860, compound

Participants

Reaction Steps

Ex. 44 (1,057 mg, 2.948 mmol) was dissolved in hydrogen bromide/glacial acetic acid (33% HBr, 70 ml). Tin powder (5.250 g, 44.2 mmol) was then added to the mixture in portions at room temperature in the course of 1 h and the mixture was stirred for a further 1 h. The mixture was then diluted with methylene chloride (250 ml). 3 N sodium hydroxide solution (750 ml) was added, while cooling. The mixture was stirred at room temperature for 20 min. After separation of the phases, the aqueous phase was extracted with methylene chloride (3×20 ml). The combined organic extracts were dried over Na2SO4 and then concentrated (976 mg of beige-coloured solid). After separation of this mixture by chromatography [silica gel 60 (100 g); ethyl acetate/methanol 10:1 (550 ml), ethyl acetate/methanol 20:3 (575 ml), ethyl acetate/methanol 5:1 (1,200 ml), ethyl acetate/methanol 3:1 (400 ml)] N,N-dimethyl-1-phenyl-4-(3-propyl-1H-indol-2-yl)cyclohexanamine (less polar diastereoisomer) (318 mg, 30%, m.p.: 177-181° C.) and the more polar diastereoisomer (267 mg, 25%, m.p.: 211-215° C.) were obtained as white and, respectively, beige-coloured solids.

Provenance & Evidence