Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclohexane | HCID 8078 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,5-Dibromothiazole | HCID 312394 | — |
| Reactant | Ethyl 4-ethyl-4-piperidinecarboxylate hydrochloride | HCID 53393421 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 66977183 | HCID 66977183 | 77.3% |
Reaction Steps
To a solution of ethyl 4-ethylpiperidine-4-carboxylate hydrochloride (140 mg, 0.62 mmol) and 2,5-dibromothiazole (100 mg, 0.41 mmol) in DMF (0.3 mL) was added triethylamine (0.26 mL, 1.9 mmol) at rt and the mixture heated to 100° C. and stirred for 2 h. The mixture was cooled to rt, diluted with EtOAc (2 mL) and MeOH (2 mL). then evaporated to dryness under reduced pressure. The crude residue was purified over 12 g silica-gel using EtOAc: cyclohexane (10% to 60%) to obtain the desired product as viscous oil (110 mg, 77% yield). MS: 347.03, 349.01 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09181234B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-b1f7b5e86d0947de8482ae1bff73231d |
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| Source note | uspto-grants-2015_11 |
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