Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidin-4-ol | HCID 79341 | — |
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | HCID 61100554 | HCID 61100554 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 70648009 | HCID 70648009 | 54.9% |
Reaction Steps
Molecular sieves, (2,4-difluorophenyl)phenylmethanol (3.69 g, 16.8 mmol), and p-toluenesulfonic acid monohydrate (3.84 g, 20.2 mmol) were added to a suspension of 4-hydroxypiperidine (1.7 g, 16.8 mmol) in toluene, and the mixture was refluxed for 3 hours while removing water using a Dean-Stark condenser. After the completion of the reaction was confirmed by HPLC, the reaction mixture was allowed to cool down to a room temperature. From the reaction mixture, the insoluble matter was removed, and then the solvent was distilled off. The resulting residue was dissolved in ethyl acetate and washed with a 2-N sodium hydroxide solution 3 times. The organic layer was dried over magnesium sulfate, and then the solvent was distilled off. Thus the title compound (2.8 g, 54.9%) was obtained as an oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09365553B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-10e749bd810a49a3876611c2992a9149 |
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| Source note | uspto-grants-2016_06 |
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