1-(cyclopenten-1-yl)ethanone

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

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 23.0 g (0.1 mole) of 6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride, 23.0 g (0.2 mole) of 1-cyclopenten-1-yl methyl ketone in 25 ml of ethanol is refluxed overnight then evaporated in vacuo. The residual oil is partitioned between water and ether after which the aqueous layer is separated and washed with ether, made basic with concentrated ammonium hydroxide solution and stirred. A sticky solid material forms which is washed with water, partially dried in vacuo, dissolved in methylene chloride, dried over sodium sulfate, filtered and evaporated. The residual material is dissolved in benzene and chromatographed on alumina eluting with benzene then with benzene-15% ethyl acetate. The solid obtained is recrystallized from benzene-hexane to give 1,2,3,3a,5,6,10b,11,12,12a-decahydro-8,9-dimethoxybenzo[a]cyclopenta[f]quinolizin-12-one, M.P. 105°-114° C. is refluxed overnight then evaporated in vacuo The residual oil is partitioned between water and ether after which the aqueous layer is separated washed with ether A sticky solid material forms which is washed with water partially dried in vacuo dissolved in methylene chloride dried over sodium sulfate filtered evaporated The residual material is dissolved in benzene chromatographed on alumina eluting with benzene The solid obtained is recrystallized from benzene-hexane

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

Procedure: A mixture of 23.0 g (0.1 mole) of 6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride, 23.0 g (0.2 mole) of 1-cyclopenten-1-yl methyl ketone in 25 ml of ethanol is refluxed overnight then evaporated in vacuo. The residual oil is partitioned between water and ether after which the aqueous layer is separated and washed with ether, made basic with concentrated ammonium hydroxide solution and stirred. A sticky solid material forms which is washed with water, partially dried in vacuo, dissolved in methylene chloride, dried over sodium sulfate, filtered and evaporated. The residual material is dissolved in benzene and chromatographed on alumina eluting with benzene then with benzene-15% ethyl acetate. The solid obtained is recrystallized from benzene-hexane to give 1,2,3,3a,5,6,10b,11,12,12a-decahydro-8,9-dimethoxybenzo[a]cyclopenta[f]quinolizin-12-one, M.P. 105°-114° C. is refluxed overnight then evaporated in vacuo The residual oil is partitioned between water and ether after which the aqueous layer is separated washed with ether A sticky solid material forms which is washed with water partially dried in vacuo dissolved in methylene chloride dried over sodium sulfate filtered evaporated The residual material is dissolved in benzene chromatographed on alumina eluting with benzene The solid obtained is recrystallized from benzene-hexane

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

Procedure: When in Example 32 appropriate amounts of 3,4-dihydro-6,7-dimethoxyisoquinoline hydrochloride and 1-chylohexen-1-yl methyl ketone respectively are substituted for 3,4-dihydroisoquinoline hydrochloride and 1-cyclopenten-1-yl methyl ketone, 2,3,4,4a,6,7,11b,12,13,13a-decahydro-9,10-dimethoxy-1H-dibenzo[a,f]quinolizin-13-one is obtained M.P. 129°-141° C.

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

Procedure: When in Example 32 appropriate amounts of 3,4-dihydro-6,7-dimethoxyisoquinoline hydrochloride and 1-chylohexen-1-yl methyl ketone respectively are substituted for 3,4-dihydroisoquinoline hydrochloride and 1-cyclopenten-1-yl methyl ketone, 2,3,4,4a,6,7,11b,12,13,13a-decahydro-9,10-dimethoxy-1H-dibenzo[a,f]quinolizin-13-one is obtained M.P. 129°-141° C.

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

Procedure: A mixture of 16.7 g (0.1 mole) of 3,4-dihydroisoquinoline hydrochloride and 27.0 g (0.02 mole) of 1-cyclopenten-1-yl methyl ketone in 22 ml of ethanol is refluxed overnight then evaporated to dryness. The remaining solid is dissolved in water and washed with ether. The aqueous layer is made basic with concentrated ammonium hydroxide solution with stirring. Upon the formation of an oil, ice is added to the mixture after which a solid is formed. The solid material is washed with water, dried overnight in a vacuum oven, and recrystallized from hexane to give 1,2,3,3a,5,6,10b,11,12,12 a-decahydrobenzo[a]cyclopenta[f]quinolizin-12-one, M.P. 101°-102.5° C. is refluxed overnight then evaporated to dryness The remaining solid is dissolved in water washed with ether Upon the formation of an oil, ice is added to the mixture after which a solid is formed The solid material is washed with water dried overnight in a vacuum oven recrystallized from hexane

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

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

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

Procedure: A solution of 11.02 g of 1-acetyl-cyclopent-1-ene in 50 ml of methanol is cooled to -10°C and mixed with 28.8 ml of perhydrol within 5 minutes. In the course of 1 hour, while stirring and cooling, 8.25 ml of 6N-sodium hydroxide solution are added, the whole is stirred for 1/2 hour at room temperature, diluted with 125 ml of water and extracted with pentane. The pentane solution is washed neutral with sodium chloride solution and the pentane is distilled off through a Vigreux column. The residue is distilled under 10 mm Hg pressure, to yield 1-acetyl-1,2-epoxy-cyclopentane passing over at 62° - 63°C. cooling the whole is stirred for 1/2 hour at room temperature extracted with pentane The pentane solution is washed neutral with sodium chloride solution the pentane is distilled off through a Vigreux column The residue is distilled under 10 mm Hg pressure

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

Procedure: When in Example 6 appropriate amounts of 3,4-dihydro-6,7 -dimethoxyisoquinoline hydrochloride and 1-cyclohexen-1-yl methyl ketone respectively are substituted for 3,4-dihydroisoquinoline and 1-cyclopenten-1-yl methyl ketone, 2,3,4,4a,6,7,11b,12,13,13a-decahydro-9,10-dimethoxy-1H-dibenzo[a,f]quinolizin-13-one is obtained, M.P. 129°-141°C.

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

Procedure: A mixture of 23.0 g (0.1 mole) of 6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride, 23.0 g (0.2 mole) of 1-cyclopenten-1-yl methyl ketone in 25 ml of ethanol is refluxed overnight then evaporated in vacuo. The residual oil is partitioned between water and ether after which the aqueous layer is separated and washed with ether, made basic with concentrated ammonium hydroxide solution and stirred. A sticky solid material forms which is washed with water, partially dried in vacuo, dissolved in methylene chloride, dried over sodium sulfate, filtered and evaporated. The residual material is dissolved in benzene and chromatographed on alumina eluting with benzene then with benzene-15% ethyl acetate. The solid obtained is recrystallized from benzene-hexane to give 1,2,3,3a,5,6,10b,11,12,12a-decahydro-8,9-dimethoxybenzo[a]cyclopenta[f]quinolizin-12-one, M.P. 105°-114° C. is refluxed overnight then evaporated in vacuo The residual oil is partitioned between water and ether after which the aqueous layer is separated washed with ether A sticky solid material forms which is washed with water partially dried in vacuo dissolved in methylene chloride dried over sodium sulfate filtered evaporated The residual material is dissolved in benzene chromatographed on alumina eluting with benzene The solid obtained is recrystallized from benzene-hexane