Dimethylformamide → HCID 71502739, compound

Participants

Reaction Conditions

Reaction Steps

94.6 g (0.3 mol) 4-(4-Cyano-3-methyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester, 87.6 mL (0.66 mol) N,N-Dimethylformamide dimethylacetal, 109 mL (1.32 mol) pyrrolidine and 60.4 mL DMF (0.78 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 h. The temperature was brought to 120° C. and kept at this temperature for 7.5 h. Heating was discontinued and the mixture was chilled to ambient temperature. Then, 200 mL water and 400 mL isopropanol were added. The mixture was stirred for 3 h at ambient temperature and 1 h at 5° C. to precipitate the product. The solid was collected rinsed with isopropanol/water (70/30) collected and dried to yield 113.7 g (yield 95.5%, purity 93.3%) of 4-[4-Cyano-3-((E)-2-pyrrolidin-1-yl-vinyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester

Provenance & Evidence