反应详情

Aqueous hydrochloric acid (0.5 mL of 12 M) and 10% palladium on carbon (0.100 g) were added to a solution of 1-benzyl-7-(3-pyridyl)-1,7-diazaspiro[4.4]nonane (1.0 g, 3.41 mmol) in methanol (30 mL). The mixture was shaken under a hydrogen atmosphere (50 psi) in a Parr hydrogenation apparatus for 24 h and filtered through Celite. The filtrate was concentrated by rotary evaporation and column chromatographed on Merck silica gel 60 (70-230 mesh). Elution with 0.01:1:9 (v/v) aqueous ammonia/methanol/chloroform, and concentration of selected fractions, gave 0.650 g (93.8%) of viscous, brown oil. A portion (300 mg, 1.48 mmol) of this material was treated with aqueous hydrochloric acid (2 mL). The water was azeotropically removed by repeated treatment with small volumes of ethanol (˜5 mL) and rotary evaporation. The resulting solid was recrystallized from hot isopropanol to give 360 mg (88.2%) of fine tan crystals.

1. filtrationfiltered through Celite
2. concentrationThe filtrate was concentrated by rotary evaporation and column
3. customchromatographed on Merck silica gel 60 (70-230 mesh)
4. washElution with 0.01:1:9 (v/v) aqueous ammonia/methanol/chloroform, and concentration of selected fractions
5. customgave 0.650 g (93.8%) of viscous, brown oil
6. customThe water was azeotropically removed
7. customwith small volumes of ethanol (˜5 mL) and rotary evaporation
8. customThe resulting solid was recrystallized from hot isopropanol