Reaktion #1470513

Reaktionsgleichung

4-methyl-1-(2-methyl-1H-indol-4-yl)piperazine

2,2,2-trichloroethyl chloroformate

sodium hydrogen carbonate

→

4-(2,2,2-trichloroethoxycarbonyl)-1-(2-methyl-1H-indol-4-yl)piperazine

Ausbeute 85.0%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction solution was cooled
2. 2
   workup.ADDITIONwere added
3. 3
   SonstigeThe organic layer was removed
4. 4
   Trocknendried (potassium carbonate)
5. 5
   Sonstigeevaporated under reduced pressure
6. 6
   SonstigeThe residue was chromatographed
7. 7
   Waschenelution with 10% ethyl acetate in hexanes

Vorschrift

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.

Quelle