4-benzoylmorpholin-3-one

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: 3-Methoxycaprolactam was prepared from 3-chlorocaprolactam (prepared as described in Francis, et al. J. Am. Chem. Soc. 1958, 80, 6238) and sodium methoxide according to the method of Kondelikova, et al. (Collect. Czech. Chem. Commun. 1971, 36(9), 3391). The desired product N-benzoyl-3-methoxycaprolactam is synthesized as for N-benzoyl-3-oxomorpholine (Example I) using 3 -methoxycaprolactam in place of morpholin-3-one.

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

Procedure: Synthesized as for N-benzoyl-3-oxomorpholine (Example I) using nonanoyl chloride (Aldrich) in place of benzoyl chloride.

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

Procedure: Synthesized as for N-benzoyl-3-oxomorpholine (Example I) using 3-aminopropanol (Aldrich) in place of 2-aminoethanol.

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

Procedure: Synthesized as for N-benzoyl-3-oxomorpholine (Example I) using 2-chloropropionic acid (Aldrich) in place of chloroacetic acid.

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 100 ml, three neck round bottom flask is equipped with a stir bar, a condenser, an addition funnel, a thermometer, and a temperature control device (Therm-O-Watch™, I2R). To this reaction flask is added the 3-oxomorpholine synthesized above (5.5 g, 0.054 moles), triethylamine (Aldrich, 6.0 g, 0.059 moles), and toluene (Baker, 15.0 g). To the addition funnel is added benzoyl chloride (Aldrich, 7.6 g, 0.054 moles). The reaction is heated to 90° C. under argon, and the benzoyl chloride is charged dropwise into the flask. After the addition is complete, the reaction is heated under reflux for 10 hours under argon as a white precipitate forms. The reaction mixture is then cooled and the precipitate is removed by vacuum filtration. Solvent is stripped from the resulting filtrate on a Kugelrohr apparatus at 2 mmHg and 70° C. for 1 hour to obtain the desired N-benzoyl-3-oxomorpholine as an oil. A 100 ml, three neck round bottom flask is equipped with a stir bar, a condenser, an addition funnel After the addition the reaction is heated under reflux for 10 hours under argon as a white precipitate forms The reaction mixture is then cooled the precipitate is removed by vacuum filtration