4-prop-2-enoxycyclohexan-1-one

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

Procedure: To a solution (100 mL) of 1H-1,2,4-triazol-3-amine (2.4 g) and 4-(prop-2-en-1-yloxy)cyclohexanone (5.3 g) in acetic acid was added sodium cyanoborohydride (9.1 g), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained reaction mixture was purified by silica gel column chromatography to give the title compound as a colorless solid (3.2 g, 50%). the solvent was evaporated under reduced pressure The obtained residue was poured into saturated aqueous sodium hydrogen carbonate the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1) The obtained extract was dried over anhydrous sodium sulfate the solvent was evaporated under reduced pressure The obtained reaction mixture was purified by silica gel column chromatography

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

Procedure: To a solution (100 mL) of 1H-1,2,4-triazol-3-amine (2.4 g) and 4-(prop-2-en-1-yloxy)cyclohexanone (5.3 g) in acetic acid was added sodium cyanoborohydride (9.1 g), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained reaction mixture was purified by silica gel column chromatography to give the title compound as a colorless solid (3.2 g, 50%). the solvent was evaporated under reduced pressure The obtained residue was poured into saturated aqueous sodium hydrogen carbonate the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1) The obtained extract was dried over anhydrous sodium sulfate the solvent was evaporated under reduced pressure The obtained reaction mixture was purified by silica gel column chromatography

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

Procedure: 15.5 g of compound (12) (100 mmole), 1.5 g (50 mmole) paraformaldehyde and 4.1 g (50 mmole) dimethylamine hydrochloride were stirred for 25 minutes in 30 ml acetic acid in a bath at 105° C. The acetic acid was distilled off under vacuum, and the residue was dissolved in 110 ml 2-butanone. Compound (13) was obtained in a yield of 77% theoretical, melting point 125° C.-127° C. The acetic acid was distilled off under vacuum the residue was dissolved in 110 ml 2-butanone

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

Procedure: 19.8 g of compound (11) (0.1 mmole) were stirred for 2 hours at room temperature with 120 ml ether and 40 ml of 6N hydrochloric acid. The mixture was then neutralised with sodium hydrogen carbonate, extracted three times with ether, and the ether solution was dried over sodium sulphate. After removing the solvent by distillation, 15.2 g of crude product were obtained; the product was purified with 3:1 diisopropyl ether/n-hexane via a silica gel column. extracted three times with ether the ether solution was dried over sodium sulphate After removing the solvent by distillation

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

Procedure: To a solution (100 mL) of 1H-1,2,4-triazol-3-amine (2.4 g) and 4-(prop-2-en-1-yloxy)cyclohexanone (5.3 g) in acetic acid was added sodium cyanoborohydride (9.1 g), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained reaction mixture was purified by silica gel column chromatography to give the title compound as a colorless solid (3.2 g, 50%). the solvent was evaporated under reduced pressure The obtained residue was poured into saturated aqueous sodium hydrogen carbonate the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1) The obtained extract was dried over anhydrous sodium sulfate the solvent was evaporated under reduced pressure The obtained reaction mixture was purified by silica gel column chromatography

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

Procedure: To a solution (100 mL) of 1H-1,2,4-triazol-3-amine (2.4 g) and 4-(prop-2-en-1-yloxy)cyclohexanone (5.3 g) in acetic acid was added sodium cyanoborohydride (9.1 g), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained reaction mixture was purified by silica gel column chromatography to give the title compound as a colorless solid (3.2 g, 50%). the solvent was evaporated under reduced pressure The obtained residue was poured into saturated aqueous sodium hydrogen carbonate the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1) The obtained extract was dried over anhydrous sodium sulfate the solvent was evaporated under reduced pressure The obtained reaction mixture was purified by silica gel column chromatography

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

Procedure: To a solution (100 mL) of 1H-1,2,4-triazol-3-amine (2.4 g) and 4-(prop-2-en-1-yloxy)cyclohexanone (5.3 g) in acetic acid was added sodium cyanoborohydride (9.1 g), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained reaction mixture was purified by silica gel column chromatography to give the title compound as a colorless solid (3.2 g, 50%). the solvent was evaporated under reduced pressure The obtained residue was poured into saturated aqueous sodium hydrogen carbonate the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1) The obtained extract was dried over anhydrous sodium sulfate the solvent was evaporated under reduced pressure The obtained reaction mixture was purified by silica gel column chromatography

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

Procedure: To a solution (100 mL) of 1H-1,2,4-triazol-3-amine (2.4 g) and 4-(prop-2-en-1-yloxy)cyclohexanone (5.3 g) in acetic acid was added sodium cyanoborohydride (9.1 g), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained reaction mixture was purified by silica gel column chromatography to give the title compound as a colorless solid (3.2 g, 50%). the solvent was evaporated under reduced pressure The obtained residue was poured into saturated aqueous sodium hydrogen carbonate the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1) The obtained extract was dried over anhydrous sodium sulfate the solvent was evaporated under reduced pressure The obtained reaction mixture was purified by silica gel column chromatography

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

Procedure: To a solution (100 mL) of 1H-1,2,4-triazol-3-amine (2.4 g) and 4-(prop-2-en-1-yloxy)cyclohexanone (5.3 g) in acetic acid was added sodium cyanoborohydride (9.1 g), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained reaction mixture was purified by silica gel column chromatography to give the title compound as a colorless solid (3.2 g, 50%). the solvent was evaporated under reduced pressure The obtained residue was poured into saturated aqueous sodium hydrogen carbonate the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1) The obtained extract was dried over anhydrous sodium sulfate the solvent was evaporated under reduced pressure The obtained reaction mixture was purified by silica gel column chromatography