3,4,5,6-tetrahydro-1H-1-benzazocin-2-one

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4.7 g of 3,4,5,6-tetrahydro-1-benzazocin-2(1H)-one, J. Chem. Soc. (C), 2176 (1969) in chloroform (75 ml), phosphorus pentachloride (5.9 g) is added in portions, while maintaining the temperature at 0°-5° C. When addition is complete, iodine (60 mg) is added, followed by bromine (4.5 g), which is added dropwise over five minutes. The mixture is then refluxed for 4 hours. The chloroform solution is evaporated and the residue partitioned between ice/water (60 ml) and dichloromethane (100 ml). The organic phase is dried over magnesium sulfate and evaporated under reduced pressure. The crude residue is purified by chromatography on silica gel, eluting with ether/hexane mixtures. Concentration of the appropriate fractions yields 3-bromo-3,4,5,6-tetrahydro-1-benzazocin-2(1H)-one. while maintaining the temperature at 0°-5° C When addition is added dropwise over five minutes The mixture is then refluxed for 4 hours The chloroform solution is evaporated the residue partitioned between ice/water (60 ml) and dichloromethane (100 ml) The organic phase is dried over magnesium sulfate evaporated under reduced pressure The crude residue is purified by chromatography on silica gel eluting with ether/hexane mixtures

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 6-acetoxy-3,4,5,6-tetrahydro-1-benzazocin-2(1H)-one (7.4 g) in ethanol (250 ml) is hydrogenated at 45 psi at 70° C. using 10% palladium on charcoal (1.5 g) as catalyst. The catalyst is filtered off and the solvent removed under reduced pressure. The residue is recrystallized from methanol/ethyl acetate to give 3,4,5,6-tetrahydro-1-benzazocin-2(1H)-one. is hydrogenated at 45 psi at 70° C. The catalyst is filtered off the solvent removed under reduced pressure The residue is recrystallized from methanol/ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 6-acetoxy-3,4,5,6-tetrahydro-1-benzazocin-2(1H)-one (7.4 g) in ethanol (250 ml) is hydrogenated at 45 psi at 70° C. using 10% palladium on charcoal (1.5 g) as catalyst. The catalyst is filtered off and the solvent removed under reduced pressure. The residue is recrystallized from methanol/ethyl acetate to give 3,4,5,6-tetrahydro-1-benzazocin-2(1H)-one. is hydrogenated at 45 psi at 70° C. The catalyst is filtered off the solvent removed under reduced pressure The residue is recrystallized from methanol/ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 6-acetoxy-3,4,5,6-tetrahydro-1-benzazocin-2(1H)-one (7.4 g) in ethanol (250 ml) is hydrogenated at 45 psi at 70° C. using 10% palladium on charcoal (1.5 g) as catalyst. The catalyst is filtered off and the solvent removed under reduced pressure. The residue is recrystallized from methanol/ethyl acetate to give 3,4,5,6-tetrahydro-1-benzazocin-2(1H)-one. is hydrogenated at 45 psi at 70° C. The catalyst is filtered off the solvent removed under reduced pressure The residue is recrystallized from methanol/ethyl acetate