90389-96-1

3-(Methylaminomethyl)benzonitrile is used as pharmaceutical intermediate.

Step 1: Anhydrous THF solution (20 mL) of 3-(bromomethyl)benzonitrile (5 g, 25.5 mmol, 1 eq.) was added to a 250 mL three-necked round-bottomed flask under nitrogen protection. A THF solution of methylamine (2 M, 63.76 mL, 127.52 mmol, 5 eq.) was added dropwise to the above solution over a period of 1 hr. The reaction mixture was stirred at room temperature for 2 hours. A small amount of bisbenzylated byproduct (7%) was observed during the reaction. Upon completion of the reaction, the mixture was filtered to remove the generated salt. The filtrate was concentrated under reduced pressure and the residue was dissolved in dichloromethane and evaporated again under reduced pressure to give N-methyl-3-cyanobenzylamine as a yellow oil (3.78 g, quantitative yield). The product could be used in the next reaction without further purification.LC/MS (Method B) showed that the molecular ion peak of the target product was 146.8 (M + H)+.

[1] Patent: WO2012/4287, 2012, A1. Location in patent: Page/Page column 93-94
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[3] Patent: WO2009/43889, 2009, A2. Location in patent: Page/Page column 166
[4] Patent: WO2010/112461, 2010, A1. Location in patent: Page/Page column 67
[5] Chemische Berichte, 1937, vol. 70, p. 1241,1249