4-(dimethylamino)cyclohexan-1-one;hydrochloride

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

Procedure: A solution of 3-benzyloxyphenylhydrazine hydrochloride (140 g.) and 4-dimethylaminocyclohexanone hydrochloride (100 g.) in 3 liters of ethyl alochol was refluxed for six hours and evaporated to dryness. The solid was suspended in 1 liter of water and filtered to give 119 g. of 3-(dimethylamino)-7-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride (Example 239). The water filtrate deposited a solid which was recrystallized from ethyl alcohol to give 38 g. of 3-(dimethylamino)-5-(benzyloxy)-1,2,3,4,-tetrahydrocarbazole hydrochloride, m.p. 207°-209° C. evaporated to dryness filtered to give 119 g was recrystallized from ethyl alcohol to give 38 g

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

Procedure: A solution of 15.8 g. of 4-dimethylaminocyclohexanone hydrochloride and 20.3 g. of 3-benzyloxyphenylhydrazine hydrochloride (m.p. 165°-168° C.) in 225 ml. of absolute ethyl alcohol was heated under reflux for three hours, cooled to room temperature, and diluted with 50 ml. of water. After standing for three hours the resulting crystals were collected by filtration and washed with ethyl alcohol to give, after recrystallization from ethyl alcohol, 6.1 g. of 3-(dimethylamino)-7-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 237°-239° C. under reflux for three hours diluted with 50 ml the resulting crystals were collected by filtration washed with ethyl alcohol to give after recrystallization from ethyl alcohol, 6.1 g

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

Procedure: A solution of 15.8 g. of 4-dimethylaminocyclohexanone hydrochloride and 20.3 g. of 3-benzyloxyphenylhydrazine hydrochloride (m.p. 165°-168° C.) in 225 ml. of absolute ethyl alcohol was heated under reflux for three hours, cooled to room temperature, and diluted with 50 ml. of water. After standing for three hours the resulting crystals were collected by filtration and washed with ethyl alcohol to give, after recrystallization from ethyl alcohol, 6.1 g. of 3-(dimethylamino)-7-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 237°-239° C. under reflux for three hours diluted with 50 ml the resulting crystals were collected by filtration washed with ethyl alcohol to give after recrystallization from ethyl alcohol, 6.1 g

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

Procedure: A solution of 3-benzyloxyphenylhydrazine hydrochloride (140 g.) and 4-dimethylaminocyclohexanone hydrochloride (100 g.) in 3 liters of ethyl alochol was refluxed for six hours and evaporated to dryness. The solid was suspended in 1 liter of water and filtered to give 119 g. of 3-(dimethylamino)-7-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride (Example 239). The water filtrate deposited a solid which was recrystallized from ethyl alcohol to give 38 g. of 3-(dimethylamino)-5-(benzyloxy)-1,2,3,4,-tetrahydrocarbazole hydrochloride, m.p. 207°-209° C. evaporated to dryness filtered to give 119 g was recrystallized from ethyl alcohol to give 38 g

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

Procedure: A solution of 15.8 g. of 4-dimethylaminocyclohexanone hydrochloride and 20.3 g. of 3-benzyloxyphenylhydrazine hydrochloride (m.p. 165°-168° C.) in 225 ml. of absolute ethyl alcohol was heated under reflux for three hours, cooled to room temperature, and diluted with 50 ml. of water. After standing for three hours the resulting crystals were collected by filtration and washed with ethyl alcohol to give, after recrystallization from ethyl alcohol, 6.1 g. of 3-(dimethylamino)-7-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 237°-239° C. under reflux for three hours diluted with 50 ml the resulting crystals were collected by filtration washed with ethyl alcohol to give after recrystallization from ethyl alcohol, 6.1 g

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

Procedure: A solution of 15.8 g. of 4-dimethylaminocyclohexanone hydrochloride and 20.3 g. of 3-benzyloxyphenylhydrazine hydrochloride (m.p. 165°-168° C.) in 225 ml. of absolute ethyl alcohol was heated under reflux for three hours, cooled to room temperature, and diluted with 50 ml. of water. After standing for three hours the resulting crystals were collected by filtration and washed with ethyl alcohol to give, after recrystallization from ethyl alcohol, 6.1 g. of 3-(dimethylamino)-7-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 237°-239° C. under reflux for three hours diluted with 50 ml the resulting crystals were collected by filtration washed with ethyl alcohol to give after recrystallization from ethyl alcohol, 6.1 g

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

Procedure: A solution of 3-benzyloxyphenylhydrazine hydrochloride (140 g.) and 4-dimethylaminocyclohexanone hydrochloride (100 g.) in 3 liters of ethyl alochol was refluxed for six hours and evaporated to dryness. The solid was suspended in 1 liter of water and filtered to give 119 g. of 3-(dimethylamino)-7-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride (Example 239). The water filtrate deposited a solid which was recrystallized from ethyl alcohol to give 38 g. of 3-(dimethylamino)-5-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 207°-209° C. evaporated to dryness filtered to give 119 g was recrystallized from ethyl alcohol to give 38 g

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

Procedure: A solution of 15.8 g. of 4-dimethylaminocyclohexanone hydrochloride and 20.3 g. of 3-benzyloxyphenylhydrazine hydrochloride (m.p. 165°-168° C.) in 225 ml. of absolute ethyl alcohol was heated under reflux for three hours, cooled to room temperature, and diluted with 50 ml. of water. After standing for three hours the resulting crystals were collected by filtration and washed with ethyl alcohol to give, after recrystallization from ethyl alcohol, 6.1 g. of 3-(dimethylamino)-7-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 237°-239° C. under reflux for three hours diluted with 50 ml the resulting crystals were collected by filtration washed with ethyl alcohol to give after recrystallization from ethyl alcohol, 6.1 g

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

Procedure: A solution of 3-benzyloxyphenylhydrazine hydrochloride (140 g.) and 4-dimethylaminocyclohexanone hydrochloride (100 g.) in 3 liters of ethyl alochol was refluxed for six hours and evaporated to dryness. The solid was suspended in 1 liter of water and filtered to give 119 g. of 3-(dimethylamino)-7-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride (Example 239). The water filtrate deposited a solid which was recrystallized from ethyl alcohol to give 38 g. of 3-(dimethylamino)-5-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 207°-209° C. evaporated to dryness filtered to give 119 g was recrystallized from ethyl alcohol to give 38 g

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

Procedure: A solution of 15.8 g. of 4-dimethylaminocyclohexanone hydrochloride and 20.3 g. of 3-benzyloxyphenylhydrazine hydrochloride (m.p. 165°-168° C.) in 225 ml. of absolute ethyl alcohol was heated under reflux for three hours, cooled to room temperature, and diluted with 50 ml. of water. After standing for three hours the resulting crystals were collected by filtration and washed with ethyl alcohol to give, after recrystallization from ethyl alcohol, 6.1 g. of 3-(dimethylamino)-7-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 237°-239° C. under reflux for three hours diluted with 50 ml the resulting crystals were collected by filtration washed with ethyl alcohol to give after recrystallization from ethyl alcohol, 6.1 g

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

Procedure: A mixture of 1.78 gm (10 mMol) of 4-dimethylaminocyclohexanone hydrochloride and 0.70 gm (10 mMol) of hydroxylamine hydrochloride in 25 mL ethanol was treated with 3 mL pyridine and then heated at reflux for 30 minutes. The reaction mixture was then cooled to room temperature and stored at 4° C. for 18 hours. The resulting crystalline solid was collected and washed with cold ethanol. The solid was then dissolved in water and the aqueous solution made basic by the addition of potassium carbonate. The aqueous phase was then extracted with dichloromethane which contained a small amount of isopropanol. The organic extracts were combined, dried over sodium sulfate and concentrated under reduced pressure to provide a crystalline solid. This solid was recrystallized from ethanol to provide 1.05 gm (67%) of the desired oxime. heated at reflux for 30 minutes The resulting crystalline solid was collected washed with cold ethanol The solid was then dissolved in water by the addition of potassium carbonate The aqueous phase was then extracted with dichloromethane which dried over sodium sulfate concentrated under reduced pressure to provide a crystalline solid This solid was recrystallized from ethanol

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

Procedure: A mixture of 1.78 gm (10 mMol) of 4-dimethylaminocyclohexanone hydrochloride and 0.70 gm (10 mMol) of hydroxylamine hydrochloride in 25 mL ethanol was treated with 3 mL pyridine and then heated at reflux for 30 minutes. The reaction mixture was then cooled to room temperature and stored at 4° C. for 18 hours. The resulting crystalline solid was collected and washed with cold ethanol. The solid was then dissolved in water and the aqueous solution made basic by the addition of potassium carbonate. The aqueous phase was then extracted with dichloromethane which contained a small amount of isopropanol. The organic extracts were combined, dried over sodium sulfate and concentrated under reduced pressure to provide a crystalline solid. This solid was recrystallized from ethanol to provide 1.05 gm (67%) of the desired oxime. heated at reflux for 30 minutes The resulting crystalline solid was collected washed with cold ethanol The solid was then dissolved in water by the addition of potassium carbonate The aqueous phase was then extracted with dichloromethane which dried over sodium sulfate concentrated under reduced pressure to provide a crystalline solid This solid was recrystallized from ethanol