Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl Alcohol | HCID 244 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 178475032 | HCID 178475032 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 178475034 | HCID 178475034 | 56.9% |
Reaction Steps
975 mg (3.06 mmol) of N-[4-(1-chloro-isoquinolin-6-yloxy)-cyclohexyl]-acetamide (18) were dissolved in 20 ml of dimethyl acetamide and 992 mg (9.17 mmol) of benzyl alcohol were added. After addition of 367 mg (9.17 mmol) of sodium hydride (60%), the reaction mixture was stirred for 3 h at room temperature and for 1 h at 80° C. Then, the solvent was removed in vacuo, the residue was dissolved in dichloromethane and washed three times with water. The organic layer was dried with magnesium sulfate and evaporated. Final purification by preparative HPLC yielded 680 mg of the title compound. Rt=1.75 min (Method B). Detected mass: 391.2 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08609691B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-863001d13d1f40ce8fa1dc1032ea32d5 |
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| Source note | uspto-grants-2013_12 |
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