HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-((4-(4-Amino-2-methoxybenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Amino-o-anisic acid | HCID 75599 | — |
| Reactant | Propylphosphonic anhydride | HCID 111923 | — |
| Reactant | N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide | HCID 66877987 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-((4-(4-Amino-2-methoxybenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide | HCID 57917689 | 32.4% |
Reaction Steps
1-Propanephosphonic acid cyclic anhydride (12.91 g, 20.2 mmol, 12.91 mL) was added dropwise to a solution of 4-amino-2-methoxybenzoic acid (1.70 g, 10.1 mmol), N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide (3.07 g, 11.2 mmol) and triethylamine (3.08 g. 30.3 mmol, 4.23 mL) in dichloromethane. The reaction was stirred at room temperature for 1 hour. The reaction was concentrated under reduced pressure and the residue was taken up with ethyl acetate, washed with water, sodium hydrogen carbonate and brine. The organic phase was concentrated under vacuum to afford the title compound (1.39 g). MS (ESI) m/z 425.4 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08314091B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-e5e790bf01a647b7ba81bc4971c95847 |
| Source note | uspto-grants-2012_11 |