Synthesis
General procedure for the synthesis of [4-(1-pyrrolidinyl)phenyl]methanamine from 4-(1-pyrrolidinyl)benzonitrile:
1. 4-(1-pyrrolidinyl)benzonitrile (1.68 g, 9.76 mmol) was dissolved in 10 mL of ether at 0 °C and slowly added dropwise to LiAlH4 (2 equiv, 742 mg) suspended in ether.
2. The reaction mixture was stirred at room temperature for 24 hours.
3. Upon completion of the reaction, water was carefully added to quench the reaction, followed by filtration and washing of the solid salt with ether.
4. The organic phase was separated and dried over anhydrous sodium sulfate, then the solvent was evaporated to give 1.48 g of a yellow oily product in 86% yield. 5. The product was subjected to 1HNMR.
5. The product was characterized by 1HNMR (DMSO, 200 MHz): δ 1.60 (2H, bs), 1.93 (4H, m), 3.17 (4H, m), 3.57 (2H, s), 6.46 (2H, d, J = 8.6 Hz), 7.09 (2H, d, J = 8.4 Hz).
References
[1] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3651 - 3660
[2] Patent: WO2011/120604, 2011, A1. Location in patent: Page/Page column 44; 45; 134
[3] Patent: EP2377850, 2011, A1. Location in patent: Page/Page column 17
