Methyl Acrylate → Methyl 3-(4-Methylpiperazin-1-yl)propanoate
Reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[CH3:7][N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1>>[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([CH2:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])[CH2:10][CH2:9]1Participants
Conditions
- Temperature
- 0 °C
Procedure
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.
Workup
- temperatureThe temperature should be maintained below 50° C.
- additionOnce the addition
- waitthe temperature adjusted to 50° C. for at least 16 hours
- temperatureto cool to ambient temperature
- customthe excess methyl acrylate is removed under vacuum
- customat ambient temperature
Sources & evidence
- ORD record
- ord-bd5e86ee7f0348989ae24377c9bde5f2
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212305B2
Reaction notes
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