2-(Phenylmethyl)-2-azabicyclo-[3.1.1]heptane-1-carbonitrile synthesis
- Product Name:2-(Phenylmethyl)-2-azabicyclo-[3.1.1]heptane-1-carbonitrile
- CAS Number:1169708-27-3
- Molecular formula:C14H16N2
- Molecular Weight:212.29
Yield:1169708-27-3 56%
Reaction Conditions:
with benzylamine in methanol; for 72 h;Reflux;
Steps:
5.a Method a:
To a solution of 3-(2-chloroethyl)cyclobutan-1 -one (p3, 4.03 g, 30.39 mmol) in Methanol (40 mL), 2-(benzylamino)-2-methylpropanenitrile (p4, 10.59 g, 60.79 mmol) and phenylmethanamine (2.19 mL, 20.06 mmol) were added and the resulting reaction mixture was stirred at reflux for 72 hrs. The mixture was concentrated and taken up with ether. The mixture was filtered, the solid was further triturated with ether and the mixture filtered. The combined organic phases were concentrated under vacuum and the crude material was purified by FC on silica gel (eluting with Cy/EA from 100/0 to 85/15) affording 2-benzyl-2-azabicyclo[3.1.1]heptane-1 -carbonitrile (p5, 3.59 g, y= 56%) as orange oil. NMR (1 H, Chloroform-d): δ ppm 7.17-7.51 (m, 5H), 3.82-3.96 (m, 2H), 2.82-2.97 (m, 2H), 2.51 -2.59 (m, 1 H), 2.41 -2.51 (m, 2H), 2.22-2.36 (m, 2H), 1 .89-2.01 (m, 2H).
References:
WO2019/81939,2019,A1 Location in patent:Page/Page column 46
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