Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methacryloyl chloride | HCID 13528 | — |
| Reactant | 1-Hydroxypiperidine | HCID 20935 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 22728695 | HCID 22728695 | 76.6% |
Reaction Steps
A few of the inventive 1-hydroxypiperidine (0.96 g, 9.49 mmol) and triethylamine (1.50 mL, 10.8 mmol) were dissolved in anhydrous dichloromethane (40 mL) and cooled to 0° C. Methacryloyl chloride (1 mL, 10.2 mmol) was then added slowly, dropwise. The reaction was then slowly warmed to room temperature. After 2.5 h, the reaction mixture was washed with deionized water (40 mL), 1 M NaOH (20 mL), deionized water (20 mL), 5% citric acid (20 mL), and brine (20 mL). After drying over sodium sulfate and filtering, the product was concentrated by rotary evaporation and dried in vacuo to give and amber liquid. Flash chromatography on silica gel, eluting with dichloromethane, followed by 1-5% methanol:dichloromethane afforded piperidin-1-yl methacrylate as an amber liquid (1.23 g, 76%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09069275B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-cb5351a2025d4ff58773ce2f19150748 |
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| Source note | uspto-grants-2015_06 |
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