1-phenylprop-2-en-1-one

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

Procedure: Benzalacetone and benzalacetophenone

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

Procedure: To a stirred suspension of sodium hydride (8.0 g) in 200 ml of dry ethyl ether was added dropwise a solution of phenylvinylketone (13.22 g) and tosylmethyl isocyanide (19.52) in 150 ml of dry methyl sulfoxide and 300 ml of dry ethyl ether at such a rate that the ether refluxed gently. After complete addition, the suspension was stirred at room temperature for 30 minutes and subsequently hydrolyzed by dropwise addition of 200 ml of water. The ether layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, 0.1N sulfuric acid, and again with water. The organic phase was dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1). The desired fractions were concentrated and the residual oil was crystallized from DCM/hexane, affording the product as crystals (7.11 g), m.p. 98°-99° C. (lit* m.p. 96°-97° C.). refluxed gently After complete addition The ether layer was separated the aqueous layer extracted with ethyl acetate The combined organic layers were washed with water, 0.1N sulfuric acid The organic phase was dried over magnesium sulfate filtered evaporated in vacuo The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1) The desired fractions were concentrated the residual oil was crystallized from DCM/hexane

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

Procedure: N-(2-benzoylethyl)-N,N,N-trimethylammonium iodide (5.0 g) was suspended in water (400 ml) and the mixture passed through the CMR (15 ml/min; 90°-95° C.; atmospheric pressure) and the hot product collected in a mixture of ice (250 g) and diethyl ether (100 ml), in a flask which was cooled in an ice bath. The ether phase was separated and the aqueous extracted with ether (3×150 ml). The pooled organic phase was dried over anhydrous sodium sulphate and evaporated to dryness, affording phenylvinyl ketone as a colourless oil (1.95 g; 94% yield) in high purity, according to the 1H NMR spectrum; cf ref.15, where a yield of 51% was obtained. passed through the CMR (15 ml/min; 90°-95° C.; atmospheric pressure) the hot product collected in a mixture of ice (250 g) and diethyl ether (100 ml), in a flask which was cooled in an ice bath The ether phase was separated the aqueous extracted with ether (3×150 ml) The pooled organic phase was dried over anhydrous sodium sulphate evaporated to dryness

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

Procedure: N-(2-benzoylethyl)-N,N,N-trimethylammonium iodide (5.0 g) was suspended in water (400 ml) and the mixture passed through the CMR (15 ml/min; 90°-95° C.; atmospheric pressure) and the hot product collected in a mixture of ice (250 g) and diethyl ether (100 ml), in a flask which was cooled in an ice bath. The ether phase was separated and the aqueous extracted with ether (3×150 ml). The pooled organic phase was dried over anhydrous sodium sulphate and evaporated to dryness, affording phenylvinyl ketone as a colourless oil (1.95 g; 94% yield) in high purity, according to the 1H NMR spectrum; cf ref.15, where a yield of 51% was obtained. passed through the CMR (15 ml/min; 90°-95° C.; atmospheric pressure) the hot product collected in a mixture of ice (250 g) and diethyl ether (100 ml), in a flask which was cooled in an ice bath The ether phase was separated the aqueous extracted with ether (3×150 ml) The pooled organic phase was dried over anhydrous sodium sulphate evaporated to dryness

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

Procedure: To a stirred suspension of sodium hydride (8.0 g) in 200 ml of dry ethyl ether was added dropwise a solution of phenylvinylketone (13.22 g) and tosylmethyl isocyanide (19.52) in 150 ml of dry methyl sulfoxide and 300 ml of dry ethyl ether at such a rate that the ether refluxed gently. After complete addition, the suspension was stirred at room temperature for 30 minutes and subsequently hydrolyzed by dropwise addition of 200 ml of water. The ether layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, 0.1N sulfuric acid, and again with water. The organic phase was dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1). The desired fractions were concentrated and the residual oil was crystallized from DCM/hexane, affording the product as crystals (7.11 g), m.p. 98°-99° C. (lit* m.p. 96°-97° C). refluxed gently After complete addition The ether layer was separated the aqueous layer extracted with ethyl acetate The combined organic layers were washed with water, 0.1N sulfuric acid The organic phase was dried over magnesium sulfate filtered evaporated in vacuo The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1) The desired fractions were concentrated the residual oil was crystallized from DCM/hexane

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

Procedure: To a stirred suspension of sodium hydride (8.0 g) in 200 ml of dry ethyl ether was added dropwise a solution of phenylvinylketone (13.22 g) and tosylmethyl isocyanide (19.52) in 150 ml of dry methyl sulfoxide and 300 ml of dry ethyl ether at such a rate that the ether refluxed gently. After complete addition, the suspension was stirred at room temperature for 30 minutes and subsequently hydrolyzed by dropwise addition of 200 ml of water. The ether layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, 0.1N sulfuric acid, and again with water. The organic phase was dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1). The desired fractions were concentrated and the residual oil was crystallized from DCM/hexane, affording the product as crystals (7.11 g), m.p. 98°-99° C. (lit* m.p. 96°-97° C). refluxed gently After complete addition The ether layer was separated the aqueous layer extracted with ethyl acetate The combined organic layers were washed with water, 0.1N sulfuric acid The organic phase was dried over magnesium sulfate filtered evaporated in vacuo The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1) The desired fractions were concentrated the residual oil was crystallized from DCM/hexane

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 1,3-dimethyl-piperidin-4-one (0.1 g, 0.787 mmol) in mixture of 1,4 dioxane (2 mL) and water (0.1 mL) was added crushed KOH (44 mg, 0.787 mmol). The reaction mixture was stirred at 25° C. for 10 min. To this was added 1-phenylprop-2-en-1-one (103 mg, 0.787 mmol) dropwise. The reaction mixture was stirred at 25° C. for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was diluted with water (10 mL) and EtOAc (20 mL), the organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified by column chromatography on neutral alumina (eluted with EtOAc:Hexanes, 1:99) to afford 1,3-dimethyl-3-(3-oxo-3-phenyl-propyl)-piperidin-4-one as an oil (22 mg). was added The reaction mixture was stirred at 25° C. for 2 h The reaction mixture was concentrated under reduced pressure the residue was diluted with water (10 mL) and EtOAc (20 mL) the organic layer was separated dried over anhydrous sodium sulfate concentrated under reduced pressure The resulting crude product was purified by column chromatography on neutral alumina (eluted with EtOAc:Hexanes, 1:99)

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

Procedure: Benzalacetone and benzalacetophenone

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

Procedure: To a stirred suspension of sodium hydride (8.0 g) in 200 ml of dry ethyl ether was added dropwise a solution of phenylvinylketone (13.22 g) and tosylmethyl isocyanide (19.52) in 150 ml of dry methyl sulfoxide and 300 ml of dry ethyl ether at such a rate that the ether refluxed gently. After complete addition, the suspension was stirred at room temperature for 30 minutes and subsequently hydrolyzed by dropwise addition of 200 ml of water. The ether layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, 0.1N sulfuric acid, and again with water. The organic phase was dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1). The desired fractions were concentrated and the residual oil was crystallized from DCM/hexane, affording the product as crystals (7.11 g), m.p. 98°-99° C. (lit* m.p. 96°-97° C.). refluxed gently After complete addition The ether layer was separated the aqueous layer extracted with ethyl acetate The combined organic layers were washed with water, 0.1N sulfuric acid The organic phase was dried over magnesium sulfate filtered evaporated in vacuo The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1) The desired fractions were concentrated the residual oil was crystallized from DCM/hexane

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

Procedure: To a stirred suspension of sodium hydride (8.0 g) in 200 ml of dry ethyl ether was added dropwise a solution of phenylvinylketone (13.22 g) and tosylmethyl isocyanide (19.52) in 150 ml of dry methyl sulfoxide and 300 ml of dry ethyl ether at such a rate that the ether refluxed gently. After complete addition, the suspension was stirred at room temperature for 30 minutes and subsequently hydrolyzed by dropwise addition of 200 ml of water. The ether layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, 0.1N sulfuric acid, and again with water. The organic phase was dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1). The desired fractions were concentrated and the residual oil was crystallized from DCM/hexane, affording the product as crystals (7.11 g), m.p. 98°-99° C. (lit* m.p. 96°-97° C.). refluxed gently After complete addition The ether layer was separated the aqueous layer extracted with ethyl acetate The combined organic layers were washed with water, 0.1N sulfuric acid The organic phase was dried over magnesium sulfate filtered evaporated in vacuo The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1) The desired fractions were concentrated the residual oil was crystallized from DCM/hexane

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

Procedure: N-(2-benzoylethyl)-N,N,N-trimethylammonium iodide (5.0 g) was suspended in water (400 ml) and the mixture passed through the CMR (15 ml/min; 90°-95° C.; atmospheric pressure) and the hot product collected in a mixture of ice (250 g) and diethyl ether (100 ml), in a flask which was cooled in an ice bath. The ether phase was separated and the aqueous extracted with ether (3×150 ml). The pooled organic phase was dried over anhydrous sodium sulphate and evaporated to dryness, affording phenylvinyl ketone as a colourless oil (1.95 g; 94% yield) in high purity, according to the 1H NMR spectrum; cf ref.15, where a yield of 51% was obtained. passed through the CMR (15 ml/min; 90°-95° C.; atmospheric pressure) the hot product collected in a mixture of ice (250 g) and diethyl ether (100 ml), in a flask which was cooled in an ice bath The ether phase was separated the aqueous extracted with ether (3×150 ml) The pooled organic phase was dried over anhydrous sodium sulphate evaporated to dryness

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

Procedure: To a stirred suspension of sodium hydride (8.0 g) in 200 ml of dry ethyl ether was added dropwise a solution of phenylvinylketone (13.22 g) and tosylmethyl isocyanide (19.52) in 150 ml of dry methyl sulfoxide and 300 ml of dry ethyl ether at such a rate that the ether refluxed gently. After complete addition, the suspension was stirred at room temperature for 30 minutes and subsequently hydrolyzed by dropwise addition of 200 ml of water. The ether layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, 0.1N sulfuric acid, and again with water. The organic phase was dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1). The desired fractions were concentrated and the residual oil was crystallized from DCM/hexane, affording the product as crystals (7.11 g), m.p. 98°-99° C. (lit*m.p. 96°-97° C.). refluxed gently After complete addition The ether layer was separated the aqueous layer extracted with ethyl acetate The combined organic layers were washed with water, 0.1N sulfuric acid The organic phase was dried over magnesium sulfate filtered evaporated in vacuo The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1) The desired fractions were concentrated the residual oil was crystallized from DCM/hexane