HuagongsheHuagongshe Chemistry Print Report · For research reference only
(1,1'-Biphenyl)-4-carboxylic acid → HCID 16812804, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (1,1'-Biphenyl)-4-carboxylic acid | HCID 66724 | — |
| Reactant | 2-(piperidin-4-yl)-1H-1,3-benzodiazole | HCID 715810 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 16812804 | HCID 16812804 | 73.2% |
Reaction Steps
To a stirred mixture of 4-biphenyl carboxylic acid (10.0 g, 50.5 mmol) and 2-(piperidin-4-yl)-1H-benzimidazole (10.1 g, 50.5 mmol) in DCM (400 mL) is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (12.0 g, 62.7 mmol) and 4-dimethylaminopyridine (3.08 g, 25.2 mmol). After 3 h the reaction mixture is diluted with saturated aqueous NaHCO3 (200 mL) and water (100 mL). The mixture is stirred for a few minutes. The organic layer is separated, washed with water, dried over Na2SO4, filtered and concentrated under reduced pressure. Trituration with EtOAc and further washing with EtOAc gives 14.1 g of [4-(1H-benzimidazol-2-yl)piperidin-1-yl](biphenyl-4-yl)methanone.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08609696B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-327e6c11082f4b369262b10e15821286 |
| Source note | uspto-grants-2013_12 |