Acetic Acid → HCID 86735972, compound

Participants

Reaction Steps

3 g (0.0063 mole) of 2β-piperidino-16β-N-methyl-piperazino-3α,17β-dihydroxy-5α-androstane (Example 11) are dissolved in the mixture of 13 ml of acetic acid anydride and 1 ml of glacial acetic acid, whereafter 0.3 g of zinc chloride is given to the solution. The reaction mixture is stirred for 12 hours, whereafter the excess acetic acid anhydride is decomposed by adding 40 ml of water. The solution is cooled to 0° to 5° C and 15% aqueous sodium hydroxide solution is added at the same temperature until the pH achieves the value of 9-10. The precipitated fluffy substance is immediately extracted with ether. The ether extract is washed with an aqueous solution saturated with sodium chloride until a neutral state is achieved. The layers are separated, the ether layer is dried over sodium sulfate and filtered. The filtrate is treated with 3 g of decolorizing silica gel, the mixture is filtered and evaporated to dryness. The product is crystallized from the residue by trituration with n-hexane, filtered and dried. Yield: 2.6 g (73.5%) of 2β-piperidino-16β-N-methyl-piperazino-3α,17β-diacetoxy-5α-androstane; m.p. 95°-98° C; [α]D25 = +33.9° (c = 1 in chloroform).

Provenance & Evidence