Hydrochloric Acid → HCID 20164994, compound

Participants

Reaction Steps

4.9 ml of diisopropylamine and 10 g of 3-(3-cyano-4-morpholino-benzoyl)propionic acid are added to a suspension of 1.7 g of a 50% dispersion of sodium hydride in 35 ml of dimethylformamide and the mixture is heated for 5 minutes to reflux temperature. Then 28.9 ml of a 1.2 molar solution of butyllithium in hexane are added dropwise at -70° . The reaction mixture is stirred for a further 10 minutes at -30° and then 2.8 ml of ethyl iodide are added at -70° . The batch is stirred for a further 20 hours at room temperature with the addition of another 5.6 ml of ethyl iodide after the first 3 hours. For working up, water is added and the pH is adjusted to 1 with 120 ml of 1N hydrochloric acid. The aqueous phase is extracted with ether and the ethereal extracts are extracted with 2N sodium carbonate solution. The sodium carbonate extracts are in turn adjusted to pH 1 and then extracted with a 1:1 mixture of ether/ethyl acetate. These extracts are washed with brine, dried over sodium sulfate and concentrated by evaporation, affording 10.5 g of crude 3-(3-cyano-4-morpholinobenzoyl)valeric acid, which is further reacted direct as described above.

Provenance & Evidence