Methyl Acrylate → Methyl 3-(4-Methylpiperazin-1-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

In a 500-mL 3-neck round bottom flask, 150.0 g (1.7 moles) of methyl acrylate is charged. The reactor is cooled to 0° C. using an ice bath. Then, 77.0 g (0.77 moles) of 1-methyl piperazine are added slowly to prevent overheating of the reaction mass. The temperature should be maintained below 50° C. by controlling the addition rate of 1-methyl piperazine. Overheating may cause polymerization of the excess methyl acrylate present in the reactor. Once the addition is completed, the mixture is agitated using a magnetic stirring bar and the temperature adjusted to 50° C. for at least 16 hours. Then, the reaction is allowed to cool to ambient temperature and the excess methyl acrylate is removed under vacuum. The final product is a light brown liquid at ambient temperature. The transformation is monitored with thin layer chromatography (TLC) using 9:1 CHCl3/MeOH. Complete conversion is apparent from the lack of olefinic protons in the 1H-NMR spectra. 1H-NMR (300 MHz, CDCl3): δ 3.20 (s, 3H), 2.12 (t, 7.3 Hz, 2H), 1.94 (m, 10H), 1.71 (s, 3H). 13C-NMR (75 MHz, CDCl3): δ 171.31, 54.00, 52.41, 51.78, 50.22, 44.92, 30.96.

Provenance & Evidence