699-04-7

To a stirred solution of 4-methylbenzyl chloride (2.5 g, 17.85 mmol) in ethanol (15 ml) was slowly added 40% aqueous methylamine (5 ml) and stirred continuously for 4 h at room temperature. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure to remove the solvent and subsequently quenched with deionized water (30 ml). The aqueous phase was extracted with dichloromethane (2 x 25 ml) and the organic phases were combined and dried with anhydrous sodium sulfate. The dried organic phase was concentrated under reduced pressure to afford N-methyl-N-(4-methylbenzyl)amine as a yellow oil (2.1 g, 87% yield).

[1] Patent: WO2009/109998, 2009, A1. Location in patent: Page/Page column 50
[2] Patent: WO2009/109999, 2009, A1. Location in patent: Page/Page column 70
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[5] Journal of Medicinal Chemistry, 1983, vol. 26, # 3, p. 309 - 312