Cyclopropanemethanamine → N-Cyclopropylmethyl-10,11-dihydro-5H-dibenzo-(a,d)-cyclohepten-5-imine

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In a Carius tube is placed 4.52 g of N-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-imine, 9.2 g of cyclopropylmethylamine and 0.46 g of p-toluenesulfonic acid hydrate. The tube is sealed under vacuum and heated to 120° for 60 hours. The cooled tube is opened, the excess cyclopropylmethylamine is removed under vacuum, and the resiude is dissolved in ether. The solution is washed with aqueous sodium hydroxide solution and dried. The solvent is removed, and the residue is combined with the recovered cyclopropylmethylamine and 0.43 g of p-toluenesulfonic acid hydrate. The mixture is transferred to a Carius tube which is then sealed under vacuum and heated to 120° for an additional 30 hours to complete the reaction. The mixture is worked up as described above, and the crude product is crystallized from hexane to give 3.47 g (65%) of N-cyclopropylmethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-imine, mp 98°-99°. An analytical sample (hexane) had mp 99°-100°. Nmr spectrum (in CDCl3): multiplets at τ 2.1-3.0 (8H), 6.1-7.5 (6H), 8.3-9.0 (1H) and 9.1-10.0 (4H). Anal. Calcd. for C19H19N: C, 87.31; H, 7.33; N, 5.36; Found: C, 87.52; H, 7.27; N, 5.53.

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