Potassium Carbonate → HCID 67239172, compound

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Reaction Steps

0.4 ml of 2,2,2-trichloroethylchloro formate and 0.52 g of K2CO3 were added to a solution of the compound obtained in Example 4.10 (1.02 g) in toluene (25 ml), kept under argon inert atmosphere. The mixture was heated at reflux for 16 hours and at the end cooled at room temperature. The mixture is washed in sequence with water, with an aqueous solution of 15% citric acid and then with brine. At the end of the washings the organic phase was recovered and dehydrated on sodium sulphate. After solvent evaporation 1.21 g of a light yellow oil (carbamate) were obtained. The oil was dissolved in 25 ml of glacial acetic acid. To the solution 0.82 g of zinc in powder were added. The mixture was kept under stirring at room temperature for 16 hours and at the end diluted with about 25 ml of toluene. The solvent was evaporated under vacuum. The residue was dissolved in the minimum volume of dichloromethane. The solution was extracted three times with an aqueous solution of 15% w citric acid. The aqueous phases were shaken with dichloromethane, then brought to an alkaline pH with conc. NH4OH and extracted again with dichloromethane. The pooled organic phases were dehydrated with sodium sulphate and the solvent evaporated. 0.52 g of the compound 4-[(3,9-diazabicyclo[4.2.1]non-3-yyl)-(3-methoxy-phenyl)methyl]-N,N-dimethylbenzamide were obtained. Yield: 62%; IR (nujol) (λ=cm−1) 1646 (C═O), 3120 (NH); 1H-NMR (CDCl3): δ 1.39-1.65 (m, 3H), 1.74-1.97 (m, 1H), 2.11-2.30 (m, 2H), 2.66 (bs, 1H), 2.75 (dd, 1H, J=2.2 and 11.0 Hz), 2.81-3.04 (m, 3H), 3.05 (s, 6H), 3.11-3.32 (m, 2H), 3.81 (s, 3H), 4.27 (s, 1H), 6.63-6.79 (m, 1H), 7.00-7.20 (m, 5H), 7.55 (d, 2H, J=8.1 Hz). Anal. calc. for C24H31N3O2: C, 73.25; H, 7.94; N, 10.68. Found: C, 73.11; H, 7.92; N, 10.65.

Provenance & Evidence