Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1,2-Dimethylpiperidin-4-one | HCID 12424039 | — |
| Reactant | HCID 66601555 | HCID 66601555 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 49779837 | HCID 49779837 | — |
Reaction Steps
To a stirred solution of 1-(4-chlorophenyl)-1-(2-(6-methylpyridin-3-yl)ethyl)hydrazine (1 g, 3.83 mmol) in dioxane (10 mL) was added 1,2-dimethylpiperidin-4-one (0.538 g, 4.59 mmol) and 0.5 mL of conc. sulfuric acid at RT. The reaction was heated at 90° C. for 2 h. After completion of reaction, the mixture was basified by addition of a saturated solution of NaHCO3. The product was extracted with EtOAc, and the organic layer washed with water, dried over sodium sulfate and concentrated. The solid obtained was purified by HPLC. 1HNMR (CD3OD, TFA salt) d (ppm): 8.30 (s, 1H), 8.05 (d, 1H), 7.64 (d, 1H), 7.50 (s, 1H), 7.24 (d, 1H), 7.10 (d, 1H), 4.50 (t, 2H), 4.40 (m, 1H), 4.0 (m, 1H), 3.80 (m, 1H), 3.30 (m, 3H), 3.0 (m, 4H), 2.62 (s, 3H), 1.50 (d, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09255094B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-e7d56978e9ec4cfd87b7977ddfe98cab |
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| Source note | uspto-grants-2016_02 |
|---|