Reaktion #502496

Reaktionsgleichung

cyclopropyl(piperazin-1-yl)methanone

3-(methoxycarbonyl)benzoic acid

1-hydroxybenzotriazole

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

methyl 3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)benzoate

Ausbeute 60.1%

Lösungsmittel

water

dichloromethane

triethyl amine

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 16 h
2. 2
   Extraktionextracted with dichloromethane (100 mL×3)
3. 3
   Waschenthe organic phase was washed with sodium bicarbonate, brine
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 20:1 to 2:1)

Vorschrift

To a solution of 3-(methoxycarbonyl)benzoic acid (0.9 g, 5 mmol) in dichloromethane (20 mL), 1-hydroxybenzotriazole (0.75 g, 5.5 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.06 g, 5.5 mmol) and triethyl amine (2 mL) were added. The mixture was stirred at room temperature for 30 min, and then cyclopropyl(piperazin-1-yl)methanone (1.0 g, 5 mmol) was added and the mixture was stirred at room temperature for 16 h. The resulting mixture was added water (50 mL) and extracted with dichloromethane (100 mL×3), the organic phase was washed with sodium bicarbonate, brine and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 20:1 to 2:1), 0.95 g of methyl 3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)benzoate as an oil was obtained, Yield 60%. 1H-NMR (400 MHz, CDCl3) 0.80-0.82 (m, 2H), 1.00-1.04 (m, 2H), 1.24-1.27 (m, 1H), 3.25-3.78 (m, 8H), 3.94 (s, 3H), 7.52-7.55 (t, J=7.6 Hz, 1H), 7.63-7.65 (d, J=7.6 Hz, 1H), 8.09-8.14 (m, 2H); LC-MS (ESI) m/z: 317 (M+1)+.

Quelle