Benzene, 1-bromo-4-(trifluoromethyl)- → HCID 68071226, compound

Participants

Reaction Conditions

Reaction Steps

A solution of piperidin-3-ylmethyl-carbamic acid tert-butyl ester (1.00 g, 4.67 mmol), 1-bromo-4-trifluoromethyl-benzene (1.15 g, 5.13 mmol), sodium tert-butoxide (673 mg, 7.00 mmol), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (291 mg, 0.47 mmol) and tris(dibenzylideneacetone)-dipalladium (0) (214 mg, 0.23 mmol) in toluene (5 mL) at 25° C. was purged with nitrogen gas and evacuated three times. The solution was sealed and heated to 120° C. for 14 h. The reaction mixture was cooled to 25° C., unsealed and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo to afford crude [1-(4-trifluoromethyl-phenyl)-piperidin-3-ylmethyl]-carbamic acid tert-butyl ester (1.5 g, 90% crude) as a light oil.

Provenance & Evidence