HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → 2-Pyridin-4-yl-1-{4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-1-yl}ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 4-Pyridineacetic acid | HCID 34228 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 4-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine hydrobromide | HCID 67166230 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-Pyridin-4-yl-1-{4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-1-yl}ethanone | HCID 58246474 | — |
Reaction Steps
200 mg (0.46 mmol) of 4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine hydrobromide, 81 mg (0.46 mmol) of pyridin-4-ylacetic acid, 202 μl (1.84 mmol) of 4-methylmorpholine, 361 mg (1.84 mmol) of EDCl and 135 mg (0.73 mmol) of HOBt are dissolved in 10 ml of THF and stirred at room temperature for 24 h. The reaction mixture is added to saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase is separated off, dried over sodium sulfate and evaporated to dryness. The crude mixture is purified by column chromatography on silica gel.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08436186B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-2fed1cc67a9a4b73a7b90901e8534fb3 |
| Source note | uspto-grants-2013_05 |