HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Formylbenzoic acid → Bavisant
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Formylbenzoic acid | HCID 12088 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| Reactant | Tert-butyl 4-(4-formylbenzoyl)piperazine-1-carboxylate | HCID 59218188 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Bavisant | HCID 16061509 | 78% |
Reaction Steps
4-(4-Formyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester. A suspension of 4-carboxybenzaldehyde (3.10 g) in CH2Cl2 was treated sequentially with piperazine-1-carboxylic acid tert-butyl ester (3.6 g), EDC (3.86 g), HOBt (2.68 g), and DMAP (˜0.020 g). After 18 h, the mixture was extracted with 1 N NaOH and then with 1 N HCl. The organic layer was dried (Na2SO4) and concentrated to give the title compound (5.11 g, 78%). MS (ESI): mass calcd. for C17H22N2O4, 318.16; m/z found, 219.3 [(M−100)+H]+. 1H NMR (CDCl3): 10.04 (s, 1H), 7.93 (d, J=8.2, 2H), 7.54 (d, J=8.1, 2H), 3.82-3.67 (m, 2H), 3.58-3.30 (m, 6H), 1.46 (s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07910582B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-5371445e1bab432aaa56ce271c65de02 |
| Source note | uspto-grants-2011_03 |