HuagongsheHuagongshe Chemistry Print Report · For research reference only
Anthranilamide → 4-[1-(2-Carbamoylphenylcarbamoyl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Anthranilamide | HCID 6942 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 2-[1-(Tert-butoxycarbonyl)piperidin-4-yl]propanoic acid | HCID 17781891 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 4-[1-(2-Carbamoylphenylcarbamoyl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester | HCID 59993324 | 53.3% |
Reaction Steps
A mixture of 4-(1-carboxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (28.6 g, 0.11 mol), 2-aminobenzamide (13.7 g, 0.1 mol), EDCI (21.3 g, 0.11 mol), HOBT (15 g, 0.11 mol) and Et3N (25 mL) in CH2Cl2 (500 mL) was stirred for 48 hr. The reaction mixture was diluted with CH2Cl2 (1000 mL) and washed with NaHCO3 (aq), the organic layer was dried with Na2SO4 and concentrated in vacuo to give the product a yellow solid (20 g, 48%) which was used directly for the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08642609B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-4605a8e3df2948349118e090ad701c52 |
| Source note | uspto-grants-2014_02 |