1-(2-Methoxyphenyl)piperazine → HCID 2741385, compound

Temperature

25 °C

To a solution of 1-(2-methoxyphenyl)piperazine (30 g) in dichloromethane (500 ml) are added triethylamine (22.9 ml) and ethyl chloroformate (15.8 ml), and the mixture is stirred at 25° C. overnight. The reaction solution is concentrated under reduced pressure, diluted with ethyl acetate, washed successively with 10% aqueous citric acid solution and saturated brine, and dried over magnesium sulfate. The solvent is evaporated under reduced pressure to give ethyl 4-(2-methoxyphenyl)piperazine-1-carboxylate. (2) To a solution of the above product (5 g) in conc. sulfuric acid (18 ml) is added conc. nitric acid (1.31 ml) at 0° C., and the mixture is stirred at around 10° C. for 2 hours. The reaction solution is poured into cold water, and the pH value thereof is adjusted to pH 3 with 2M aqueous sodium hydroxide solution. The resulting precipitates are collected by filtration to give ethyl 4-(2-methoxy-5-nitrophenyl)piperazine-1-carboxylate. (3) The above product (5 g) is dissolved in a mixture of methanol (50 ml) and tetrahydrofuran (50 ml), and thereto is added 2M aqueous sodium hydroxide solution (50 ml), and the mixture is heated under reflux for 18 hours. The reaction solution is diluted with water and ethyl acetate, and the organic layer is washed with saturated brine, dried over magnesium sulfate. To the organic layer is added a 30% solution of hydrogen chloride in ethanol, and the resulting precipitates are collected by filtration to give the title compound (3.52 g).

1. concentrationThe reaction solution is concentrated under reduced pressure
2. additiondiluted with ethyl acetate
3. washwashed successively with 10% aqueous citric acid solution and saturated brine
4. dry with materialdried over magnesium sulfate
5. customThe solvent is evaporated under reduced pressure

ORD record

ord-d9f047545b24494c99c2ace88543f30d

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07176199B2