Cyanide → HCID 68144827, compound

Participants

Reaction Steps

The starting material for preparing compounds of the present invention is, preferably, 1-methyl-lumilysergol-10-methylether or 1,6-dimethyl-8β-hydroxymethyl-10α-methoxyergoline (I), described and claimed in the Bernardi et al. U.S. Pat. No. 3,228,943. It is reacted at a temperature between 40° and 50° C with the chloride of an aryl- or alkylsulphonic-acid, such as tosyl chloride or mesyl chloride, in pyridine and in the presence of pyridinium chloride, to give the corresponding 8-chloromethyl derivative. This compound, that is, 1,6-dimethyl-8β-chloromethyl-10α-methoxyergoline (II), is treated with an alkaline cyanide, such as sodium or potassium cyanide in a suitable solvent, such as dimethylsulphoxide, at the temperature of 100°-120° C for a period between 4 and 8 hours. The product thus formed, that is, 1,6-dimethyl-8β-cyanomethyl-10α-methoxyergoline (III), is isolated and characterized: it has never been described in the previous literature. This product is subjected to alkaline hydrolysis, preferably with potassium hydroxide in water/ethanol/dioxan solution, under reflux conditions for a few hours.

Provenance & Evidence