Water → 9-Benzyl-9,10-diazatricyclo[4.2.1.12,5]decane

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Reaction Steps

3.44 grams of the azide (1.1A) obtained in Ex. 1.1 are dissolved in 26 ml of anhydrous THF. To this solution 2.96 grams of triphenylphosphine, dissolved in 10 ml of anhydrous THE are added. The mixture is heated at reflux for 5 hours. At the end it is cooled at room temperature and 0.5 ml of water are added. It is further heated at reflux for 14 hours and then cooled at room temperature. The precipitate is filtered under vacuum and washed with THF, suspended in 50 ml of a CH2Cl2/H2O (1/1 v/v) mixture and treated with a 10% by weight K2CO3 aqueous solution up to pH 8. The organic phase is separated, dehydrated with sodium sulphate, filtered and evaporated under vacuum. 2.13 g of 9-benzyl-9,10-diazatricyclo[4.2.1.12,5]decane are recovered. Yield: 91%. 1H-NMR (CDCl3) δ 1.45-1.55 (m, 2H); 1.80-1.90 (m, 4H); 2.00-2.15 (m, 2H); 2.78-2.88 (m, 2H); 3.02-3.12 (m, 2H); 3.31 (s, 2H); 7.20-7.45 (m, 5H). Anal, calc. for C15H20N2: C, 78.90; H, 8.83; N, 12.27. Found: C, 78.71; H, 8.80; N, 12.25.

Provenance & Evidence