Thionyl Chloride → 3,5-Dimethoxy-2-methyl-N-(3-chloro-tricyclo[3.3.1.13,7]dec-1ylmethyl)-benzamide

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Reaction Steps

A mixture of 3,5-dimethoxy-2-methylbenzoic acid from Example 67 a) (0.15 g) and thionyl chloride (2 ml) was heated to reflux temperature for 2 minutes before cooling to room temperature and concentratedunder reduced pressure. The residue was dissolved in dichloromethane (1 ml) and added to a solution of 1-adamantanemethylamine (0.104 g) in dichloromethane (5 ml) and triethylamine (1 ml) and the resulting reaction mixture stirred for 2 days. The reaction was partitioned between dichloromethane (100 ml) and aqueous hydrochloric acid (0.5M, 50 ml). The organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate (50 ml), dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by HPLC over a Dynamax® column eluting with iso-hexane: ethyl acetate (4:1) to give the title compound as a colourless solid (0.090 g).

Provenance & Evidence