Triethylamine → HCID 18326812, compound

Participants

Reaction Conditions

Reaction Steps

10.1 g (0.1 mol) of 4-hydroxypiperidine and 11 g (0.11 mol) of triethylamine are placed in 200 ml ethyl acetate and 250 ml tetrahydrofuran and a solution of 23.3 g (0.11 mol) of 2,2,2-trichloroethyl chloroformate is added dropwise at 0-4° C. The mixture is stirred for 1 hour at 0° C. and for 1 hour at ambient temperature. The precipitate is suction filtered, the filtrate is combined at −12 to −14° C. with 12 g (0.105 mol) of methanesulphonic acid chloride and at −8 to −12° C. 12 g (0.12 mol) of triethylamine in 50 ml tetrahydrofuran are added dropwise. It is stirred for 40 minutes at −10° C., the cooling bath is removed and the mixture is stirred for 30 minutes. After washing with water and saturated saline solution it is dried with magnesium sulphate, concentrated by evaporation, the residue is triturated with diisopropylether and suction filtered. 32.4 g (91.5% of theory) of 4-methanesulphonyloxy-N-2,2,2-trichlorethoxycarbonylpiperidine are obtained as colourless crystals, melting point 93° C.

Provenance & Evidence