4-[(10-benzyl-9,10-diazatricyclo-[4.2.1.12,5]dec-9-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide → 4-[(9,10-diazatricyclo[4.2.1.12,5]dec-9-yl)-(3-methoxy phenyl)methyl]-N,N-diethylbenzamide

Participants

Reaction Steps

0.38 mmoles of the compound 4-[(10-benzyl-9,10-diazatricyclo[4.2.1.12,5]-dec-9-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide obtained in Example 4.1 were mixed with palladium at 10% by weight on carbon (0.1 equivalents) in ethanol (5 ml). The mixture was submitted to hydrogenation at a pressure of 45 psi of H2 and at a temperature of 60° C., for 6 hours. At the end of the reaction the catalyst was removed by filtration under vacuum. The solvent was then evaporated under vacuum obtaining the compound 4-[(9,10-diazatricyclo[4.2.1.12,5]dec-9-yl)-(3-methoxy phenyl)methyl]-N,N-diethylbenzamide. Yield: quantitative. IR (nujol) (λ=cm−1) 1630 (C═O), 3200 (NH); 1H-NMR (CDCl3) δ 1.00-1.45 (m, 6H); 1.90-2.43 (m, 10H); 2.90-3.10 (m, 2H); 3.10-3.30 (m, 2H); 3.40-3.60 (m, 2H); 3.66 (bs, 1H); 3.79 (s, 3H); 4.26 (s, 1H); 6.75-6.80 (m, 1H); 7.03-7.38 (m, 5H); 7.60 (d, 2H, J=8.0 Hz). Anal. calc. for C27H35N3O2: C, 74.79; H, 8.14; N, 9.69. Found: C, 75.04; H, 8.13; N, 9.67.

Provenance & Evidence