HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 4-Iodo-3-methoxy-N-(1-methylpiperidin-yl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 4-Amino-1-methylpiperidine | HCID 2737531 | — |
| Reactant | tert-Butyloxy 4-Iodo-3-methoxybenzoate | HCID 86653099 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-Iodo-3-methoxy-N-(1-methylpiperidin-yl)benzamide | HCID 66688078 | 74.2% |
Reaction Steps
A solution of tert-butyloxy 4-iodo-3-methoxybenzoate (250 mg, 0.90 mmol) in anhydrous dimethylformamide (8 mL) was treated with N-ethyl-N,N-diisopropylamine (0.63 mL, 3.6 mmol) and TBTU (404 mg, 1.26 mmol). The mixture was then treated with 1-methylpiperidin-4-amine (0.160 mL, 1.26 mmol). The reaction mixture was stirred at room temperature for 24 h. The reaction was diluted with water and the resulting precipitate was collected by filtration to afford the title compound (250 mg, 71% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08846701B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-0c9e7cf7d3ff4f94af6359c374cf9327 |
| Source note | uspto-grants-2014_09 |