1-(cyclohexen-1-yl)propan-1-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 16.75 g (0.1 mole) of 3,4dihydroisoquinoline hydrochloride and 28.0 g (0.2 mole) of 1-cyclohexen-1-yl ethyl ketone in 28 ml of ethanol is refluxed for 52 hours then poured into 300 ml of water and extracted with ether. The aqueous layer is separated and made basic by slowly adding ammonium hydroxide solution with stirring. Stirring is continued until a solid is formed after which the liquid is decanted. The solid is washed with water, dissolved in methylene chloride, dried over sodium sulfate and concentrated to an oil. The oil is dissolved in refluxing hexane, filtered and concentrated to a solid which is recrystallized from hexane-benzene to give 2,3,4,4a,6,7,11b,12,13,13a-decahydro-12-methyl-1H-dibenzo[a,f]-quinolizin-13-one, M.P. 144.5°-147.5° C. is refluxed for 52 hours extracted with ether The aqueous layer is separated Stirring is formed after which the liquid is decanted The solid is washed with water dissolved in methylene chloride dried over sodium sulfate concentrated to an oil The oil is dissolved in refluxing hexane filtered concentrated to a solid which is recrystallized from hexane-benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: when in Example 1 an appropriate amount of 3,4-dihydro-6-methylisoquinoline hydrochloride and 1-cyclohexen-1-yl methyl ketone are substituted for 3,4-dihydroisoquinoline hydrochloride and 1-cyclohexen-1-yl ethyl ketone respectively, 2,3,4,4a,6,7,11b,12,13,13a-decahydro-9-methyl-1H-dibenzo[a,f]quinolizin-13-one is obtained, M.P. 101°-121°C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 16.75 g (0.1 mole) of 3,4-dihydroisoquinoline hydrochloride and 28.0 g of (0.2 mole) of 1-cyclohexen-1-yl ethyl ketone in 28 ml of ethanol is refluxed for 52 hours then poured into 300 ml of water and extracted with ether. The aqueous layer is separated and made basic by slowly adding ammonium hydroxide solution with stirring. Stirring is continued until a solid is formed after which the liquid is decanted. The solid is washed with water, dissolved in methylene chloride, dried over sodium sulfate and concentrated to an oil. The oil is dissolved in refluxing hexane, filtered, concentrated and cooled to give a solid which is recrystallized from hexane-benzene to give 2,3,4,4a,6,7,11b,12,13,13a-decahydro-12-methyl-1H-dibenzo[a,f]quinolizin-13-one, M.P. 144.5°-147.5°C. is refluxed for 52 hours extracted with ether The aqueous layer is separated Stirring is formed after which the liquid is decanted The solid is washed with water dissolved in methylene chloride dried over sodium sulfate concentrated to an oil The oil is dissolved in refluxing hexane filtered concentrated cooled to give a solid which is recrystallized from hexane-benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 16.75 g (0.1 mole) of 3,4dihydroisoquinoline hydrochloride and 28.0 g (0.2 mole) of 1-cyclohexen-1-yl ethyl ketone in 28 ml of ethanol is refluxed for 52 hours then poured into 300 ml of water and extracted with ether. The aqueous layer is separated and made basic by slowly adding ammonium hydroxide solution with stirring. Stirring is continued until a solid is formed after which the liquid is decanted. The solid is washed with water, dissolved in methylene chloride, dried over sodium sulfate and concentrated to an oil. The oil is dissolved in refluxing hexane, filtered and concentrated to a solid which is recrystallized from hexane-benzene to give 2,3,4,4a,6,7,11b,12,13,13a-decahydro-12-methyl-1H-dibenzo[a,f]-quinolizin-13-one, M.P. 144.5°-147.5° C. is refluxed for 52 hours extracted with ether The aqueous layer is separated Stirring is formed after which the liquid is decanted The solid is washed with water dissolved in methylene chloride dried over sodium sulfate concentrated to an oil The oil is dissolved in refluxing hexane filtered concentrated to a solid which is recrystallized from hexane-benzene