Benzene, (2-bromoethoxy)- → (1R,3R)-3-(2-hydroxy-2,2-dithiophen-2-yl-acetoxy)-1-methyl-1-(2-phenoxy-ethyl)-piperidinium bromide

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Reaction Steps

Hydroxy-di-thiophen-2-yl-acetic acid (R)-1-methyl-piperidin-3-yl ester (0.57, 0.00169 mol) is dissolved in acetonitrile (3 ml) at 60° C. and 2-phenoxyethyl bromide (0.51 g, 0.00254 mol) in Acetonitrile (1 ml) is added dropwise. The reaction mixture is refluxed for 96 hours, cooled to room temperature and left in the refrigerator. This gives an approximately 1:1 mixture of isomers (1R/S,3R)-3-(2-hydroxy-2,2-dithiophen-2-yl-acetoxy)-1-methyl-1-(2-phenoxy-ethyl)-piperidinium bromide (97a). The suspension is filtered off and washed with cold acetonitrile to yield (1R,3R)-3-(2-hydroxy-2,2-dithiophen-2-yl-acetoxy)-1-methyl-1-(2-phenoxy-ethyl)-piperidinium bromide (97b) as a white solid.

Provenance & Evidence