The solution of syn-3-benzyl-1,5,7-trimethyl-3,7-diazabicyclo[3.3.1]nonane-9-ol (200 mg, 0,73 mmol) in 20 mL of acetonitrile was mixed with the solution of bis-benzonitrile palladium dichloride (280 mg, 0.73 mmol) in 5 mL of the same solvent. Triethylamine (0.06 mL, 0.73 mmol) was added to the stirred solution. After 24 h at ambient temperature a dark grey precipitate of the prooduct had formed which was isolated by filtration and dried in air. Yield 220 mg (67%).

The ligand, palladium(II) chloride and its benzonitrile complex (m.p. 121-127 C) were synthesised in our laboratory.

1H NMR (dmso-d6, δ, ppm, J/Hz): 0.82 (s, 6H, 2CH3); 2.15 (d., 2H, H4a, H2a, J = 11.34); 2.40 (s, 3Н, N-CH3); 2.72 (d, 2H, H4e, H2e, J = 11.34); 3.02 (d, 1H, H9, J = 5.26); 3.20 (m, 4H, H6a, H8a, H6e, H4e); 4.06 (s, 2H, CH2Ar); 5.38 (d, 1H, ОH, J = 5.26); 6.70 (m, 1H, Ph); 6.82 (m, 2H, Ph), 7.50 (дd 1H, Ph, J = 7.35). IR (cm-1): 3436.68 (OH). Found (%): C, 45.36; H, 5.87; N, 6.42. C17H26N2OCl2Pd. Calc. (%): C, 45,13; H, 5,97; N, 6,19.

Ligand precursor: Sergey Z. Vatsadze et al.  Russ. J. Org. Chem, 2006, 42, 8, 1225-1231 http://dx.doi.org/10.1134/S1070428006080215
Ortho-palladation: Sergey Z. Vatsadze, Alexey V. Medved'ko et al. Organometallics, 2009, 28 (4), pp 1027–1031 http://dx.doi.org/10.1021/om8006695

Bis-benzonitrile palladium diclhoride: Gordon K. Anderson, Minren Lin. Inorg. Synth. 28: pp.60–63. 1990 http://dx.doi.org/10.1002/9780470132593.ch13