Chloroacetyl chloride → 2-Chloro-1-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)ethanone

Temperatur

0 °C

To as stirred solution of 1-(2,2,2-trifluoroethyl)piperazine dihydrochloride (181.6 mg, 753 μmol) and triethylamine (182 mg, 250 μL, 1.79 mmol) in dichloromethane (5 mL) cooled to 0° C., 2-chloroacetyl chloride (85.1 mg, 60.0 μL, 753 μmol) was added drop-wise over 2 min then stirred for 10 min. The reaction mixture was warmed to 25° C. over 3 h. The reaction mixture was partitioned between saturated sodium bicarbonate solution (25 mL) and dichloromethane (25 mL). The organic layer was separated, washed with water (25 mL) and brine (50 mL), dried over sodium sulfate, and concentrated to give 2-chloro-1-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)ethanone (123.3 mg, 504 μmol, 67%) as an orange oil. 1H NMR (DMSO-d6) δ: 4.73 (br. s, 2H), 3.45 (br. s, 4H), 3.23 (q, J=10.3 Hz, 2H), 2.61 (d, J=20.8 Hz, 4H).

1. temperatureThe reaction mixture was warmed to 25° C. over 3 h
2. customThe reaction mixture was partitioned between saturated sodium bicarbonate solution (25 mL) and dichloromethane (25 mL)
3. customThe organic layer was separated
4. washwashed with water (25 mL) and brine (50 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated

ORD-Eintrag

ord-d51ff873f0594437b7180e0c666a1793

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08658646B2