Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Phenylpiperidine | HCID 107207 | — |
| Reactant | Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate | HCID 86665647 | — |
| Solvent | Bicarbonate Ion | HCID 769 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 50995369 | HCID 50995369 | 33% |
Reaction Steps
A mixture of methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.104 g; 0.312 mmol), 3-phenylpiperidine (0.151 g; 0.937 mmol) and triethylamine (0.220 mL; 1.56 mmol) in tetrahydrofuran (2 mL) was heated to 110° C. in a sealed tube for 5 h. The reaction mixture was diluted with a saturated solution of hydrogen carbonate and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-15%) in heptane furnished 0.047 g (33%) of the title compound as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08906906B2 |
|---|
| Source dataset | uspto-grants-2014_12 |
|---|
| ORD ID | ord-b05dbf84171b4df4a12fca61fd9910a2 |
|---|
| Source note | uspto-grants-2014_12 |
|---|