反应详情

A mixture of (+)-3-((αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide monohydrochloride (8.22 g, 17.1 mmol, Example 1) and 5.45 g (2.5 mmol) of 5% palladium on charcoal in 160 ml of methanol:water/3:1 was heated at reflux for 20 hours. The reaction mixture was filtered through Celite under nitrogen and the filtrate was evaporated. The residue was diluted with water and the pH was adjusted to 8 with aqueous 1M sodium hydroxide. The mixture was extracted with ethyl acetate, dried over sodium sulfate, and evaporated to give 5.05 g (75%) of (+)-3-((αR)-α-((2S,5R)-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethyl-benzamide as a light yellow solid. NMR (DMSO-d6, 200 MHz): δ 1.1 (m, 12H); 2.0 (m, 1H); 2.6-2.9 (m, 3H); 3.0-3.5 (m, 7H); 5.25 (s, 1H); 6.7 (m, 3H); 7.2 (m, 3H); 7.4 (m, 2H); 9.5 (s, 1H). [α]D20 =+11.9° (abs ethanol, c=2.3). Titration of 0.20 g of product with ethanolic hydrogen chloride in ethanol solution to pH 3.5 and precipitation from dichloromethane with diethyl ether gave 0.103 g (47% recovery) of the monohydrochloride salt as an off-white solid. Calc. for C24H33N3O2HCl 0.75 H2O: C, 64.70; H, 8.03; N, 9.43; Cl, 7.96. Found: C, 64.97; H, 7.97; N, 9.38; Cl, 8.04. Mass spectrum (CI--CH4) m/e 396 (M+1, 38%); 282 (39%); 115 (100%).

1. temperatureat reflux for 20 hours
2. filtrationThe reaction mixture was filtered through Celite under nitrogen
3. customthe filtrate was evaporated
4. additionThe residue was diluted with water
5. extractionThe mixture was extracted with ethyl acetate
6. dry with materialdried over sodium sulfate
7. customevaporated