Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclohexylamine | HCID 7965 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | HCID 67821791 | HCID 67821791 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67821850 | HCID 67821850 | 16.1% |
Reaction Steps
A stirred suspension of crude potassium 4-(1H-benzimidazylmethyl)benzoate (0.49 g, 1.7 mmol) in dry DMF (10 ml) under argon was treated with cyclohexylamine (0.2 g, 2.0 mmol) and triethylamine (0.34 g, 3.4 mmol). The solution was cooled to -5° C. and DPPA (0.53 g, 1.9 mmol) in DMF (10 ml) was added. The solution was allowed to warm to room temperature, stirred overnight and concentrated to give the crude product. Chromatography (silica gel, ethyl acetate) followed by crystallisation from toluene gave N-cyclohexyl 4-(1H-benzimidazylmethyl)benzamide (91 mg, 16%) as a white crystalline solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05314880 |
|---|
| Source dataset | uspto-grants-1994_05 |
|---|
| ORD ID | ord-d7e49bb98baa45dda207ffc652e21ca5 |
|---|
| Source note | uspto-grants-1994_05 |
|---|