HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thiomorpholine → Methyl 1-(thiomorpholin-4-ylcarbonyl)-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thiomorpholine | HCID 67164 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-Methyl 1-(4-nitrophenyl) 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-1,3-dicarboxylate | HCID 58116490 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | Methyl 1-(thiomorpholin-4-ylcarbonyl)-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylate | HCID 58116476 | — |
Reaction Conditions
| Temperature | 150 °C |
|---|
Reaction Steps
A solution of 10.3 g (17.9 mmol, purity 81%) of the compound from Example 43A in 1-methyl-2-pyrrolidone (65 ml) was admixed with 12.6 ml (13.7 g, 132 mmol) of thiomorpholine and 11.5 ml (8.56 g, 66.2 mmol) of N,N-diisopropylethylamine and then heated in 5 portions in a single-mode microwave (Emrys Optimizer) at 150° C. for 1 h. For workup, the reaction solutions were combined and purified directly by means of preparative HPLC. Yield: 5.63 g (71% of theory)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08440657B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-da8fb8756a594c708152ac85f7cea7a7 |
| Source note | uspto-grants-2013_05 |