2,2,2-Trichloroethyl chloroformate → HCID 21187589, compound

Participants

Reaction Steps

A solution of 4-methyl-1-(2-methyl-1H-indol-4-yl)piperazine (0.510 g, 2.22 mmol) and 2,2,2-trichloroethyl chloroformate (5 mL) was heated at 100-110° C. for 48 hours. The reaction solution was cooled, and methylene chloride (200 mL) followed carefully by a saturated solution of sodium hydrogen carbonate (20 mL) were added. The organic layer was removed, dried (potassium carbonate), and evaporated under reduced pressure. The residue was chromatographed using silica gel (approximately 300 g) using elution with 10% ethyl acetate in hexanes to afford 4-(2,2,2-trichloroethoxycarbonyl)-1-(2-methyl-1H-indol-4-yl)piperazine as a white amorphous solid (0.74 g, 1.89 mmol, 85%): FAB LRMS (m/z, relative intensity) 394 (9), 392 (27), 390 ([MH+ with 35Cl], 32), 358 (18), 356 (29), 216 (99), 194 (100). This compound was used directly as outlined below.

Provenance & Evidence