HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethyl Sulfoxide → (3S)-N-(4-oxocyclohexyl)-1-phenylpiperidine-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | Bromobenzene | HCID 7961 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | (S)-Ethyl piperidine-3-carboxylate hydrochloride | HCID 45074034 | — |
| Reactant | (S)-1-Phenylpiperidine-3-carboxylic acid | HCID 66743624 | — |
| Product | (3S)-N-(4-oxocyclohexyl)-1-phenylpiperidine-3-carboxamide | HCID 11688042 | — |
Reaction Steps
A solution of ethyl (3S)-piperidine-3-carboxylate hydrochloride (0.1 g, 0.0005 mol), bromobenzene (0.16 g, 0.0010 mol) and potassium tert-butoxide (0.12 g, 0.0010 mol) in dimethyl sulfoxide (4 mL, 0.06 mol) was heated at 200° C. for 10 min. under microwave irradiation. The crude (3S)-1-phenylpiperidine-3-carboxylic acid was subjected to BOP-mediated coupling by using a procedure that was analogous to that described for the synthesis of example 129, step 3. LCMS: m/z 301.2 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08071624B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-eca37b3f9f8e4189a14085bb5fb2d5d3 |
| Source note | uspto-grants-2011_12 |