HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → 1-[(5-Hydroxy-2-pyridinyl)carbonyl]-piperidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 5-Hydroxypyridine-2-carboxylic acid | HCID 268740 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Ammonia | HCID 222 | 5% |
| Product | 1-[(5-Hydroxy-2-pyridinyl)carbonyl]-piperidine | HCID 44515454 | 90% |
Reaction Steps
To a solution of 5-hydroxy-2-pyridine carboxylic acid (2.00 g, 14.0 mmol) and piperidine (1.5 mL, 15 mmol) in DCM (150 mL) was added HOBt (2.80 g, 21.0 mmol), EDC (4.00 g, 21.0 mmol), and N-methyl morpholine (8.5 mL, 84 mmol). After 18 h the reaction mixture was concentrated. Chromatography of the residue (SiO2; 5-10% 2 M NH3 in MeOH/DCM) gave the title compound as a solid (1.30 g, 43%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07423147B2 |
| Source dataset | uspto-grants-2008_09 |
| ORD ID | ord-985f1f5d40da4132a25e0a2f3b49fa42 |
| Source note | uspto-grants-2008_09 |