Sodium Hydroxide → HCID 24951512, compound

Participants

Reaction Steps

Ex. 254 (350 mg, 0.86 mmol) was dissolved in hydrogen bromide/glacial acetic acid (33% HBr, 18 ml). Tin powder (1.02 g, 8.6 mmol) was then added to the mixture in portions at room temperature in the course of 40 min. A yellow suspension was formed. The mixture was stirred for a further 20 h. The mixture was then diluted with methylene chloride (50 ml) and rendered alkaline with 5 N sodium hydroxide solution (50 ml), while cooling with ice. The phases were separated. The aqueous phase was extracted with methylene chloride (3×30 ml). The combined organic phases were dried with Na2SO4 and then filtered. The volatile constituents of the filtrate were removed completely in vacuo. A pale yellow solid (534 mg) remained. This was separated by chromatography [silica gel 60 (50 g); ethyl acetate/methanol 4:1 (500 ml); methanol/ethyl acetate 3:2 (500 ml); 4:1 (500 ml)]. It was possible for N-methyl-1-phenyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine (less polar diastereoisomer) (178 mg, 50%, m.p.: 251-256° C.) and the more polar diastereoisomer (97 mg, 28%, m.p.: 224-227° C.) to be obtained in this way.

Provenance & Evidence