Synthesis
General procedure for the synthesis of 4-[2-(pyrrolidin-1-yl)ethoxy]aniline from 1-(2-(4-nitrophenoxy)ethyl)pyrrolidine: 1-[2-(4-nitrophenoxy)ethyl]pyrrolidine (purchased from CombiBlocks, LLC, 5.00 g, 0.0212 mol) was dissolved in 100 mL of methanol and 0.5 g of 10% Pd/C catalyst, and the hydrogenation reaction was carried out under a hydrogen atmosphere (using a balloon to provide hydrogen pressure) and the reaction continued overnight. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to dryness, the resulting product was used directly in the next step of the reaction without further purification (Yield: 4.36 g, Yield: 99.88%). Spectral analysis of the product showed LCMS (M + H) 207.4.
References
[1] Patent: WO2009/64835, 2009, A1. Location in patent: Page/Page column 168
[2] Patent: WO2004/26823, 2004, A1. Location in patent: Page 36
[3] Patent: WO2016/34642, 2016, A1. Location in patent: Page/Page column 35
[4] Patent: US2015/336982, 2015, A1. Location in patent: Paragraph 0155; 0157
[5] Journal of Organic Chemistry, 1951, vol. 16, p. 1421,1424
