Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 22258852 | HCID 22258852 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 22258899 | HCID 22258899 | 92% |
Reaction Steps
To a stirred solution of tert-butyl 3-{6-[2-(benzyloxy)phenyl]-2-bromo-3-cyano-4-pyridinyl}-1-piperidinecarboxylate (0.300 g, 0.547 mmol) in DMSO were added triethylamine (0.229 mL, 1.341 mmol) and benzylamine (0.147 g, 1.367 mmol). The mixture was stirred at 70° C. for 12 hrs. After cooled to room temperature, the reaction mixture was quenched with water and extracted with ethyl acetate. The separated organic phase was washed with brine, dried over Na2SO4, filtrated, and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-2/1) to give tert-butyl 3-{6-[2-(benzyloxy)phenyl]-2-benzylamino-3-cyano-4-pyridinyl}-1-piperidinecarboxylate as a yellow amorphous. (0.290 g, yield; 92%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06562811B1 |
|---|
| Source dataset | uspto-grants-2003_05 |
|---|
| ORD ID | ord-599653e63e0942c8a8022932a9feb9eb |
|---|
| Source note | uspto-grants-2003_05 |
|---|