2-(dimethylamino)cyclohexan-1-ol

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: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: To tetrahydrofuran (100 mL), oily sodium hydride (purity 60% by weight, 18 g, 450 mmol) was added and 2-(dimethylamino)ethanol (16.1 g, 180 mmol) was added dropwise at 0° C., and then the mixture was refluxed for 3 hours. To this suspension, toluene (80 mL) and tetrahydrofuran (25 mL) were added. A toluene (200 mL)/tetrahydrofuran (25 mL) mixed solution of p-toluenesulfonyl chloride (37.2 g, 195 mmol) was added dropwise at 0 to 5° C., followed by stirring at the same temperature for 1 hour. After further stirring for 1 hour under heating at reflux, the mixture was left standing to cool to room temperature. After adding dropwise 2-(dimethylamino)cyclohexanol (21.5 g, 150 mmol) at room temperature, potassium iodide (29.9 g, 180 mmol) was added. After stirring for 9 hours under heating at reflux, the reaction solution was left standing to cool to room temperature. Water was added and the solution was extracted with ethyl acetate, and then the organic phase was washed with water and saturated saline. This organic phase was dried over an anhydrous magnesium sulfate powder and then concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain 2.3 g (in a yield of 7%) of the objective compound as a yellow liquid. the mixture was refluxed for 3 hours was added dropwise at 0 to 5° C. After further stirring for 1 hour under heating at reflux the mixture was left After stirring for 9 hours under heating at reflux the reaction solution was left to cool to room temperature the solution was extracted with ethyl acetate the organic phase was washed with water and saturated saline This organic phase was dried over an anhydrous magnesium sulfate powder concentrated under reduced pressure The residue was distilled under reduced pressure

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

Procedure: To tetrahydrofuran (100 mL), oily sodium hydride (purity 60% by weight, 18 g, 450 mmol) was added and 2-(dimethylamino)ethanol (16.1 g, 180 mmol) was added dropwise at 0° C., and then the mixture was refluxed for 3 hours. To this suspension, toluene (80 mL) and tetrahydrofuran (25 mL) were added. A toluene (200 mL)/tetrahydrofuran (25 mL) mixed solution of p-toluenesulfonyl chloride (37.2 g, 195 mmol) was added dropwise at 0 to 5° C., followed by stirring at the same temperature for 1 hour. After further stirring for 1 hour under heating at reflux, the mixture was left standing to cool to room temperature. After adding dropwise 2-(dimethylamino)cyclohexanol (21.5 g, 150 mmol) at room temperature, potassium iodide (29.9 g, 180 mmol) was added. After stirring for 9 hours under heating at reflux, the reaction solution was left standing to cool to room temperature. Water was added and the solution was extracted with ethyl acetate, and then the organic phase was washed with water and saturated saline. This organic phase was dried over an anhydrous magnesium sulfate powder and then concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain 2.3 g (in a yield of 7%) of the objective compound as a yellow liquid. the mixture was refluxed for 3 hours was added dropwise at 0 to 5° C. After further stirring for 1 hour under heating at reflux the mixture was left After stirring for 9 hours under heating at reflux the reaction solution was left to cool to room temperature the solution was extracted with ethyl acetate the organic phase was washed with water and saturated saline This organic phase was dried over an anhydrous magnesium sulfate powder concentrated under reduced pressure The residue was distilled under reduced pressure

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

Procedure: A solution comprising 5 g of 2-dimethylamino-1-cyclohexanol, 10 g of 1-bromooctane and 5 ml of dimethylformamide was heated in a glass pressure bottle at about 95° for 16 hours. p-Xylene (25 ml) was added and the solution was concentrated at 60° using a film evaporator to remove dimethylformamide as its azeotrope with xylene. A second 25 ml portion of p-xylene was added and the azeotrope distilled until the residue was free of volatile material. This residue was dissolved in water, and the aqueous solution was extracted five times with diethyl ether. The aqueous solution was then concentrated under reduced pressure to give (2-hydroxycyclohexyl)(dimethyl)octylammonium bromide, a clear amorphous gum. was heated in a glass pressure bottle at about 95° for 16 hours the solution was concentrated at 60° a film evaporator to remove dimethylformamide as its azeotrope with xylene A second 25 ml portion of p-xylene was added the azeotrope distilled until the residue This residue was dissolved in water the aqueous solution was extracted five times with diethyl ether The aqueous solution was then concentrated under reduced pressure

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

Procedure: A mixture of 50.0 g of cyclohexene oxide and 100 ml of 25 percent aqueous dimethylamine was heated with stirring at 145° in a small autoclave for 8 hours. While the mixture was being concentrated to dryness at 50° on a film evaporator, absolute ethanol was added periodically to aid in removal of water. The residue was distilled through a Nester-Faust spinning band column to give 53.0 g of 2-dimethylamino-1-cyclohexanol, b.p. 64.1 - 64.2/2.4 mm. The ir curve was consistent with the assigned structure. was heated While the mixture was being concentrated to dryness at 50° on a film evaporator, absolute ethanol was added periodically to aid in removal of water The residue was distilled through a Nester-Faust