Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Methylpiperidine | HCID 69381 | — |
| Reactant | 5-Chloro-2-nitroaniline | HCID 74218 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 68384944 | HCID 68384944 | 110% |
Reaction Steps
4-Methylpiperidine (172 mg, 1.738 mmol) was added to a solution of 5-chloro-2-nitroaniline (200 mg, 1.159 mmol) in NMP (5 mL) in the presence of triethylamine (0.404 mL, 2.90 mmol). The reaction mixture was heated via microwave irradiation to 100° C. for 1 h, and. Upon cooling, the solvent was removed by vacuum. Purification by flash column chromatography (5% CH3OH/CH2Cl2) afforded the title compound (300 mg) as a solid. 1H NMR: (400 MHz, CDCl3): δ 7.98 (d, 1H, J=10.0 Hz), 6.26 (dd, 1H, J=2.8 and 10.0 Hz), 6.13 (bs, 2H), 5.92 (d, 1H, J=2.0 Hz), 3.85 (m, 2H), 2.89 (m, 2H), 1.72 (m, 2H), 1.62 (m, 1H), 1.23 (m, 2H), 0.96 (d, 3H, J=6.8 Hz).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08569511B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-91f15d0263b3405eb2bd32aa7122d3e3 |
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| Source note | uspto-grants-2013_10 |
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