5-chloro-2,3-dihydroinden-1-one

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

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

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

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

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

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

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-chloroindanone (10.2 g, supplied by Lancaster Chemicals) and 1-(3-aminopropyl)imidazole (7.62 g) was heated at 90° C., while bubbling nitrogen through the molten mixture, for 2 hours. The mixture was cooled and dissolved in absolute ethanol (140 ml). Sodium borohydride (4.63 g) was added to the solution and the mixture boiled under reflux for 7 hours. The solvent was removed under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate to give an oil which was dissolved in ether and filtered. The filtrate was treated with ethereal hydrogen chloride to give a solid which was collected and recrystallised from propan-2-ol/ethanol/water (150 ml/150 ml/trace) (with a charcoal hot filtration) to give N-(5-chloroindan-1-yl)-3-(imidazol-1-yl)propylamine dihydrochloride, m.p. 251-254° C. while bubbling nitrogen through the molten mixture The mixture was cooled dissolved in absolute ethanol (140 ml) Sodium borohydride (4.63 g) was added to the solution under reflux for 7 hours The solvent was removed under reduced pressure Water was added to the residue the mixture was extracted with ethyl acetate to give an oil which filtered The filtrate was treated with ethereal hydrogen chloride to give a solid which was collected recrystallised from propan-2-ol/ethanol/water (150 ml/150 ml/trace) ( with a charcoal hot filtration)

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

Procedure: To a mixture of 8.0 g of 5-chloroindanone and 4.2 ml of dimethylcarbonate in 60 ml of THF was added 4.0 g of 60% NaH and the mixture was heated to reflux under N2 overnight. After this time the reaction was cooled to room temperature and 4.0 ml of methyl iodide was added and the mixture was reheated to reflux overnight. The reaction was then cooled and partitioned between ether and 5% aqueous NaHCO3 and the aqueous extracts were washed twice with ether. The combined aqueous extracts were dried over MgSO4 and concentrated to 11.24 g of a brown oil. Chromatogrpahy on silica gel (10% ethyl acetate/hexane) afforded 4.25 g of the title compound as a brown oil. the mixture was heated to reflux under N2 overnight to reflux overnight The reaction was then cooled partitioned between ether and 5% aqueous NaHCO3 the aqueous extracts were washed twice with ether The combined aqueous extracts were dried over MgSO4 concentrated to 11.24 g of a brown oil

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-chloroindanone (10.2 g, supplied by Lancaster Chemicals) and 1-(3-aminopropyl)imidazole (7.62 g) was heated at 90° C., while bubbling nitrogen through the molten mixture, for 2 hours. The mixture was cooled and dissolved in absolute ethanol (140 ml). Sodium borohydride (4.63 g) was added to the solution and the mixture boiled under reflux for 7 hours. The solvent was removed under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate to give an oil which was dissolved in ether and filtered. The filtrate was treated with ethereal hydrogen chloride to give a solid which was collected and recrystallised from propan-2-ol/ethanol/water (150 ml/150 ml/trace) (with a charcoal hot filtration) to give N-(5-chloroindan-1-yl)-3-(imidazol-1-yl)propylamine dihydrochloride, m.p. 251-254° C. while bubbling nitrogen through the molten mixture The mixture was cooled dissolved in absolute ethanol (140 ml) Sodium borohydride (4.63 g) was added to the solution under reflux for 7 hours The solvent was removed under reduced pressure Water was added to the residue the mixture was extracted with ethyl acetate to give an oil which filtered The filtrate was treated with ethereal hydrogen chloride to give a solid which was collected recrystallised from propan-2-ol/ethanol/water (150 ml/150 ml/trace) ( with a charcoal hot filtration)

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 25 g of 5-chloro-1-indanone, 31 ml of 3-buten-2-ol and 250 mg of p-toluenesulfonic acid in 31 ml of 2,2-dimethoxy-propane and 250 ml of anhydrous toluene was boiled under reflux for 17 hours. The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/diethyl ether 5:1). 11.9 g (36%) of (RS)-2-(2-buten-1-yl)-5-chloro-1-indanone were obtained as a yellow oil. under reflux for 17 hours The reaction mixture was subsequently concentrated in a vacuum purified by column chromatography on silica gel (hexane/diethyl ether 5:1)