HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 4-(4-Boc-aminopiperidin-1-yl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | (Pyridin-4-yl)boronic acid | HCID 2734379 | — |
| Reactant | Tert-butyl 1-aminopiperidine-4-carboxylate | HCID 21899493 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-(4-Boc-aminopiperidin-1-yl)pyridine | HCID 69890083 | 90% |
Reaction Steps
The mixture of 4-pyridineboronic acid (0.97 g, 7.8 mmol), 4-Boc-aminopiperidine (3.25 g, 15.8 mmol), Cu(OAc)2 (2.88 g, 15.8 mmol), DMAP (catalytic amount), pyridine (2.5 mL, 32 mmol), 4A activated molecular sieve in 50 mL dry DCM was stirred for over 2 days. It was diluted with DCM, filtered through celite. It was washed with brine and water, dried, filtered through a silica plug, evaporated in vacuuo to give 4-(4-Boc-aminopiperidin-1-yl)pyridine in 90% yield. ES-MS: (+H) 278.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06632815B2 |
| Source dataset | uspto-grants-2003_10 |
| ORD ID | ord-81c103d1ec7547f2a469529aae0b410b |
| Source note | uspto-grants-2003_10 |