Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Picolyl chloride hydrochloride | HCID 23392 | — |
| Reactant | HCID 57949296 | HCID 57949296 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 57949324 | HCID 57949324 | 65% |
Reaction Steps
To a mixture of 2-chloromethylpyridine hydrochloride salt (16.9 mg, 0.103 mmol), 7-methyl-5-piperidin-4-ylmethyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (50.0 mg, 0.120 mmol) and potassium carbonate (71.2 mg, 0.515 mmol) was added acetonitrile (3.0 mL). The mixture was allowed to stir at room temperature overnight. Water (2.0 mL) was added and the product was extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated. Column chromatography provided the title compound as a yellow oil (34.1 mg, 65%). 1H NMR (300 MHz, CDCl3): δ 8.56 (d, 1H), 7.65 (t, 1H), 7.34 (m, 3H), 7.18 (m, 3H), 6.98 (d, 2H), 4.76 (s, 2H), 4.20 (s, 2H), 3.64 (s, 2H), 2.90 (d, 2H), 2.73 (s, 3H), 2.57 (d, 2H), 2.03 (t, 2H), 1.62 (m, 2H), 1.35 (m, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07968570B2 |
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| Source dataset | uspto-grants-2011_06 |
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| ORD ID | ord-8c9a343fd1bc4c059b53fa189d2def23 |
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| Source note | uspto-grants-2011_06 |
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