Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 19367002 | HCID 19367002 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 19366931 | HCID 19366931 | 92% |
Reaction Steps
NaH (158 mg, 6.56 mmol) was added to 4-(2,5-difluorophenyl)-4-hydroxymethyl-1-methylpiperidine (1.45 g, 6.56 mmol) in DMF (20 mL). The slurry was heated to 90° C. for 6 h. The reaction was diluted with hexane (200 mL), washed with water (200 mL), brine (50 mL), dried (MgSO4), and concentrated to yield 1.21 g (92%) of the title compound as a white crystalline solid; 1H NMR (400 MHz, CDCl3) δ 6.98 (dd, 1H), 6.54 (dt, 1H), 6.48 (dd, 1H), 4.37 (s, 2H), 2.84 (m, 2H), 2.31 (s, 3H), 1.97 (4H, pentuplet), 1.71 (m, 2H) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05962462 |
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| Source dataset | uspto-grants-1999_10 |
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| ORD ID | ord-4d44ed8eb1c544b39c2ef3e62b983734 |
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| Source note | uspto-grants-1999_10 |
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