HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-tert-Butylaniline → 4-[4-(3-Tert-butyl-phenylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-tert-Butylaniline | HCID 79334 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 4-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acid | HCID 2795508 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-[4-(3-Tert-butyl-phenylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester | HCID 59318017 | 35.2% |
Reaction Steps
A mixture of 3-tert-butyl aniline (117 mg, 0.78 mmol), 4-(4-carboxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (prepared as described in Biog. Med. Chem. 2006, 14, 2089) (200 mg, 0.65 mmol), EDCl (375 mg, 0.95 mmol) and a catalytic amount of DMAP in CH2Cl2 was stirred at room temperature overnight. The next day the mixture was partitioned between EtOAc and water. The organic layer was collected, dried over Na2SO4, filtered and concentrated. The residue was chromatographed with silica gel column amd 0-30% EtOAc in hexanes gradient to afford the product (100 mg, Yield: 35%). HRMS m/z calcd for C26H35N3O3 [M+H]+: 438.2751. Found: 438.2753.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08324385B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-296db7b4338f47059a2aa523136c82ba |
| Source note | uspto-grants-2012_12 |