N-cyclohexyl-3-oxobutanamide

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

Procedure: A mixture of 36.6 g of N-cyclohexyl-acetylacetamide, 32 g of methyl orthoformate, 100 ml of methanol and 1 g of p-toluene sulfonic acid was stirred for 4 hours at 25° C. and after the addition of 2 g of quinoline, the mixture was evaporated to dryness under reduced pressure. The residue was added to isopropyl ether and the mixture was cooled and vacuum filtered. The recovered precipitate was dried to obtain 40 g of N-cyclohexyl-3,3-dimethoxy-butyramide melting at 66° C. the mixture was evaporated to dryness under reduced pressure The residue was added to isopropyl ether the mixture was cooled vacuum filtered The recovered precipitate was dried

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 500 ml of benzene and 99 g of cyclohexyl amine were introduced over 30 minutes to 84 g of diketene and after stirring for 4 hours at 20° C., the mixture was evaporated to dryness by distillation under reduced pressure. The residue was taken up in isopropyl ether and the solution was cooled and vacuum filtered. The recovered precipitate was dried and crystallized from isopropyl ether to obtain 137 g of N-cyclohexyl-acetylacetamide melting at 74° C. the mixture was evaporated to dryness by distillation under reduced pressure the solution was cooled vacuum filtered The recovered precipitate was dried crystallized from isopropyl ether

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 23.6 g (0.24 mol) of cyclohexylamine in 50 ml tetrahydrofuran was added dropwise to a solution of 20 g of diketene (0.24 mol) in 200 ml tetrahydrofuran at −5 to 0° C. After 1 h stirring at 0° C. no more starting material was detected by thin layer chromatography. The reaction mixture was evaporated and the residue is recrystallized from 100 ml of ethyl acetate. This gave 30.0 g (0.16 mol, 69% yield) of a white solid. The reaction mixture was evaporated the residue is recrystallized from 100 ml of ethyl acetate

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

Procedure: 24 parts (by weight) of α-acetoxypropionaldehyde is stirred with 36.6 parts of acetoacetic cyclohexylamide and 1 part of concentrated H2SO4 in 100 parts of toluene for 3 hours at 50° C. After the mixture has been cooled to room temperature it is washed with sodium hydrogen carbonate. The organic phase is dried with Na2SO4 and concentrated to dryness. There is obtained 41 parts of 2,5-dimethylfuran-3-carboxylic cyclohexylamide having a melting point of 111° to 113° C. After recrystallization from cyclohexane the compound melts at 114° to 115° C. is washed with sodium hydrogen carbonate The organic phase is dried with Na2SO4 concentrated to dryness

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

Procedure: 24 parts (by weight) of α-acetoxypropionaldehyde is stirred with 36.6 parts of acetoacetic cyclohexylamide and 1 part of concentrated H2SO4 in 100 parts of toluene for 3 hours at 50° C. After the mixture has been cooled to room temperature it is washed with sodium hydrogen carbonate. The organic phase is dried with Na2SO4 and concentrated to dryness. There is obtained 41 parts of 2,5-dimethylfuran-3-carboxylic cyclohexylamide having a melting point of 111° to 113° C. After recrystallization from cyclohexane the compound melts at 114° to 115° C. is washed with sodium hydrogen carbonate The organic phase is dried with Na2SO4 concentrated to dryness

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

Procedure: A mixture of 36.6 g of N-cyclohexyl-acetylacetamide, 32 g of methyl orthoformate, 100 ml of methanol and 1 g of p-toluene sulfonic acid was stirred for 4 hours at 25° C. and after the addition of 2 g of quinoline, the mixture was evaporated to dryness under reduced pressure. The residue was added to isopropyl ether and the mixture was cooled and vacuum filtered. The recovered precipitate was dried to obtain 40 g of N-cyclohexyl-3,3-dimethoxy-butyramide melting at 66° C. the mixture was evaporated to dryness under reduced pressure The residue was added to isopropyl ether the mixture was cooled vacuum filtered The recovered precipitate was dried

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

Procedure: A mixture of 36.6 g of N-cyclohexyl-acetylacetamide, 32 g of methyl orthoformate, 100 ml of methanol and 1 g of p-toluene sulfonic acid was stirred for 4 hours at 25° C. and after the addition of 2 g of quinoline, the mixture was evaporated to dryness under reduced pressure. The residue was added to isopropyl ether and the mixture was cooled and vacuum filtered. The recovered precipitate was dried to obtain 40 g of N-cyclohexyl-3,3-dimethoxy-butyramide melting at 66° C. the mixture was evaporated to dryness under reduced pressure The residue was added to isopropyl ether the mixture was cooled vacuum filtered The recovered precipitate was dried

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 500 ml of benzene and 99 g of cyclohexyl amine were introduced over 30 minutes to 84 g of diketene and after stirring for 4 hours at 20° C., the mixture was evaporated to dryness by distillation under reduced pressure. The residue was taken up in isopropyl ether and the solution was cooled and vacuum filtered. The recovered precipitate was dried and crystallized from isopropyl ether to obtain 137 g of N-cyclohexyl-acetylacetamide melting at 74° C. the mixture was evaporated to dryness by distillation under reduced pressure the solution was cooled vacuum filtered The recovered precipitate was dried crystallized from isopropyl ether

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

Procedure: A solution of diketene (42 g.) in benzene (74 ml.) is added dropwise with vigorous stirring to a solution of cyclohexylamine (49.6 g.) in benzene (125 ml.). The rate of addition is adjusted so that a gentle reflux is maintained. The benzene is removed under vacuum and the yellow oil crystallizes upon trituation with hexane. A yield of 88.7 g. of product melting at 66°-69° C. is obtained. The rate of addition a gentle reflux is maintained The benzene is removed under vacuum the yellow oil crystallizes upon trituation with hexane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 23.6 g (0.24 mol) of cyclohexylamine in 50 ml tetrahydrofuran was added dropwise to a solution of 20 g of diketene (0.24 mol) in 200 ml tetrahydrofuran at −5 to 0° C. After 1 h stirring at 0° C. no more starting material was detected by thin layer chromatography. The reaction mixture was evaporated and the residue is recrystallized from 100 ml of ethyl acetate. This gave 30.0 g (0.16 mol, 69% yield) of a white solid. The reaction mixture was evaporated the residue is recrystallized from 100 ml of ethyl acetate

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

Procedure: 24 parts (by weight) of α-acetoxypropionaldehyde is stirred with 36.6 parts of acetoacetic cyclohexylamide and 1 part of concentrated H2SO4 in 100 parts of toluene for 3 hours at 50° C. After the mixture has been cooled to room temperature it is washed with sodium hydrogen carbonate. The organic phase is dried with Na2SO4 and concentrated to dryness. There is obtained 41 parts of 2,5-dimethylfuran-3-carboxylic cyclohexylamide having a melting point of 111° to 113° C. After recrystallization from cyclohexane the compound melts at 114° to 115° C. is washed with sodium hydrogen carbonate The organic phase is dried with Na2SO4 concentrated to dryness

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

Procedure: A mixture of 36.6 g of N-cyclohexyl-acetylacetamide, 32 g of methyl orthoformate, 100 ml of methanol and 1 g of p-toluene sulfonic acid was stirred for 4 hours at 25° C. and after the addition of 2 g of quinoline, the mixture was evaporated to dryness under reduced pressure. The residue was added to isopropyl ether and the mixture was cooled and vacuum filtered. The recovered precipitate was dried to obtain 40 g of N-cyclohexyl-3,3-dimethoxy-butyramide melting at 66° C. the mixture was evaporated to dryness under reduced pressure The residue was added to isopropyl ether the mixture was cooled vacuum filtered The recovered precipitate was dried