HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 4-(5-Fluoro-4-methyl-2-nitro-phenylamino)piperidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Chloro-2-fluoro-5-nitrotoluene | HCID 87593 | — |
| Reactant | 4-Amino-1-Boc-piperidine | HCID 1268291 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-(5-Fluoro-4-methyl-2-nitro-phenylamino)piperidine-1-carboxylic acid tert-butyl ester | HCID 58852279 | 18.2% |
Reaction Conditions
| Temperature | 180 °C |
|---|
Reaction Steps
A mixture of 1-chloro-5-fluoro-4-methyl-2-nitro-benzene (2 g, 10.55 mmol), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (2.32 g, 11.58 mmol), and iPr2NEt (3.8 mL) was heated for 2 hours at 180° C. by microwave heating. After cooling, the reaction mixture was diluted with CH2Cl2 and then filtered. The volatiles were removed under reduced pressure and the residue was purified by flash chromatography (25% ethyl acetate in hexanes) to afford 4-(5-fluoro-4-methyl-2-nitro-phenylamino)piperidine-1-carboxylic acid tert-butyl ester (0.68 g, 18%) as a brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07803816B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-2baa627bd70b408b9964623461bffd6c |
| Source note | uspto-grants-2010_09 |