Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Bromomethylnaphthalene | HCID 70320 | — |
| Reactant | N-Cyclopropyl-N-4-piperidinylbenzenesulfonamide | HCID 2735904 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57664577 | HCID 57664577 | 15.2% |
Reaction Steps
N-Cyclopropyl-N-piperidin-4-yl-benzenesulfonamide (56 mg, 0.2 mmol) was dissolved in DMF (2.5 ml) and triethylamine (75 μL, 54 mg, 0.54 mmol) added, followed by 2-bromomethyl-naphthalene (88 mg, 0.4 mmol). The reaction mixture was stirred for 12 hours at 80° C. and then the solvent was evaporated. The residue was purified by flash chromatography to give 12.8 mg of the desired product N-cyclopropyl-N-[1-(naphth-2-ylmethyl)-piperidin-4-yl]benzenesulfonamide (15). 1H NMR (CDCl3): δ 8.06-7.71 (m, 7H), 7.61-7.44 (m, 5H), 3.94-3.84 (m, 1H), 3.68 (S, 2H), 3.01-2.94 (m, 2H), 2.18-1.94 (m, 5H), 1.58-1.49 (m, 2H), 1.02-0.96 (m, 2H), 0.81-0.74 (m, 2H). MS (EI): m/z 421 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09000174B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-39e5609e1ae447f3bed8e995e05cc9f2 |
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| Source note | uspto-grants-2015_04 |
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