Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 2-Chloro-6-nitrobenzoic acid | HCID 79287 | — |
| Reactant | 1-Benzyl-4-piperidylamine | HCID 415852 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 21102222 | HCID 21102222 | 85.1% |
Reaction Steps
2-Chloro-6-nitro-benzoic acid (1.2 g, 5.97 mmol), 4-amino-1-benzylpiperidine (1.1 mL, 5.97 mmol), 1-hydroxybenzotriazole (0.84 g, 1.05 equiv) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide (1.1 g, 1.05 equiv) were combined in ethyl acetate (20 mL). To this solution was added triethylamine (2.5 mL. 3.0 equiv) and the reaction mixture stirred at 40° C. for 2 h. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water (2×), 5% sodium bicarbonate, brine (2×), dried over sodium sulfate, and concentrated to afford 1.9 g (85%) of the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07220862B2 |
|---|
| Source dataset | uspto-grants-2007_05 |
|---|
| ORD ID | ord-61f62479fca94563a015a0e4a5645bbb |
|---|
| Source note | uspto-grants-2007_05 |
|---|