5-methylazepan-2-one

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

Procedure: 4,4' -Dimethyl-1,1'-peroxydicyclohexylamine (5 g.) derived from the reaction of 4-methylcyclohexanone, hydrogen peroxide and ammonia) was added to a solution of sodium methoxide in methanol (1 g. of sodium in 20 c.c. methanol) and the mixture heated under reflux for 2 hours when very little peroxide remained unreacted. The product was worked up as in Example 17 to give, on distillation, 4-methylcyclohexanone (2.2 g.), 4-methyl-caprolactam (2.2 g.), b.p. 145°-150°/15 mm, and residue (0.3 g.). The structure of the lactam was confirmed by I.R. and N.M.R. spectra. the mixture heated

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

Procedure: 4,4' -Dimethyl-1,1'-peroxydicyclohexylamine (5 g.) derived from the reaction of 4-methylcyclohexanone, hydrogen peroxide and ammonia) was added to a solution of sodium methoxide in methanol (1 g. of sodium in 20 c.c. methanol) and the mixture heated under reflux for 2 hours when very little peroxide remained unreacted. The product was worked up as in Example 17 to give, on distillation, 4-methylcyclohexanone (2.2 g.), 4-methyl-caprolactam (2.2 g.), b.p. 145°-150°/15 mm, and residue (0.3 g.). The structure of the lactam was confirmed by I.R. and N.M.R. spectra. the mixture heated

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

Procedure: 4,4' -Dimethyl-1,1'-peroxydicyclohexylamine (5 g.) derived from the reaction of 4-methylcyclohexanone, hydrogen peroxide and ammonia) was added to a solution of sodium methoxide in methanol (1 g. of sodium in 20 c.c. methanol) and the mixture heated under reflux for 2 hours when very little peroxide remained unreacted. The product was worked up as in Example 17 to give, on distillation, 4-methylcyclohexanone (2.2 g.), 4-methyl-caprolactam (2.2 g.), b.p. 145°-150°/15 mm, and residue (0.3 g.). The structure of the lactam was confirmed by I.R. and N.M.R. spectra. the mixture heated

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-methylazepan-2-one (1.6 g) and dimethyl sulfate (2 g, 15.9 mmol) was stirred at 120° C. for 4 h. After it was cooled to room temperature, the reaction mixture was diluted with 10 mL ether and adjusted to pH 6 with aqueous KOH. The mixture was extracted with ether (2×50 mL). The organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration, the crude (E)-7-methoxy-4-methyl-3,4,5,6-tetrahydro-2H-azepine (1.2 g) was used for the next step without further purification. After it was cooled to room temperature The mixture was extracted with ether (2×50 mL) The organic layer was washed with brine dried over anhydrous sodium sulfate After filtration and concentration the crude (E)-7-methoxy-4-methyl-3,4,5,6-tetrahydro-2H-azepine (1.2 g) was used for the next step without further purification

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-methylcyclohexanone oxime in 5 mL 80% H2SO4 was added dropwise to H2SO4 (80%, 5 mL) while stirring and the reaction temperature was maintained at 120° C. with an external oil bath. An exotherm was observed. After 5 min, the reaction was removed from the oil bath and allowed to cool to room temperature. The reaction mixture was diluted with water (30 mL) and adjusted to pH 6 with concentrated NH4OH. This solution was further diluted with water (30 mL) and extracted with DCM (2×25 mL). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate. After filtration and concentration, the crude product (1.6 g) was used for the next step without further purification. the reaction was removed from the oil bath to cool to room temperature The reaction mixture was diluted with water (30 mL) This solution was further diluted with water (30 mL) extracted with DCM (2×25 mL) The combined organic layer was washed with brine dried over anhydrous sodium sulfate After filtration and concentration the crude product (1.6 g) was used for the next step without further purification

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

Procedure: 4,4' -Dimethyl-1,1'-peroxydicyclohexylamine (5 g.) derived from the reaction of 4-methylcyclohexanone, hydrogen peroxide and ammonia) was added to a solution of sodium methoxide in methanol (1 g. of sodium in 20 c.c. methanol) and the mixture heated under reflux for 2 hours when very little peroxide remained unreacted. The product was worked up as in Example 17 to give, on distillation, 4-methylcyclohexanone (2.2 g.), 4-methyl-caprolactam (2.2 g.), b.p. 145°-150°/15 mm, and residue (0.3 g.). The structure of the lactam was confirmed by I.R. and N.M.R. spectra. the mixture heated