HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chloride → 1-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperidin-4-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chloride | HCID 312 | — |
| Reactant | 4-Piperidone | HCID 33721 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-(((R)-oxiran-2-yl)methoxy)-2-methylbenzo[d]thiazole | HCID 21023606 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 1-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperidin-4-one | HCID 58714335 | — |
Reaction Steps
To a solution of 5-[((2R)oxiran-2-yl)methoxy]-2-methylbenzothiazole (2.0 g, 9.25 mmol) and piperidin-4-one, chloride (1.25 g, 9.25 mmol) in ethanol was added diisopropylethylamine (1.6 ml, 9.0 mmol). The mixture was heated to reflux for 16 hours. The solvent was removed and the residue purified by column chromatography (10:1 DCM:MeOH) followed by preparative TLC (10:1 DCM:MeOH) to yield 1-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperidin-4-one.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07452889B2 |
| Source dataset | uspto-grants-2008_11 |
| ORD ID | ord-63229c9e639d4418bc595bd7232a6e9d |
| Source note | uspto-grants-2008_11 |