Dimethylformamide → HCID 71502739, compound

Participants

Reaction Conditions

Reaction Steps

47.3 g (0.15 mol) 4-(4-Cyano-3-methyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester, 43.8 mL (0.33 mol) N,N-Dimethylformamide dimethylacetal, 54.6 mL (0.66 mol) pyrrolidine and 30.2 mL DMF (0.39 mol) were mixed and the mixture was heated within 30 min to 90° C. and kept at this temperature for 1 h. All volatile content was allowed to distil off. The temperature was raised to 110° C. and kept at this temperature for 2.5 h. The temperature was brought to 120° C. and kept at this temperature for 5 h. Heating was discontinued and the mixture was chilled to ambient temperature, diluted with 400 mL MTB ether and washed twice with 200 mL saturated aqueous NaHCO3 and once with 200 mL water. The organic layer was concentrated and recrystallized from isopropanol/water (245 mL/105 mL) collected and dried to yield 55.5 g (yield 93%, purity 100%) of 4-[4-Cyano-3-((E)-2-pyrrolidin-1-yl-vinyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester

Provenance & Evidence