HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Ammonia
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 14637769 | HCID 14637769 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Ammonia | HCID 222 | — |
| Product | 8-Chloro-11-(piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-6-ol | HCID 14637770 | — |
Reaction Steps
Mix the title compound of Example 1, (0.29 g, 0.893 mmol) in CH3OH (14 mL) at 0° C. under an argon atmosphere. Add NaBH4 (165 mg, 4.36 mmol) in 3 portions. After 30 minutes, pour the mixture into water and extract (3X) with CH2Cl2. Combine the organic portions, wash once with brine, dry over sodium sulfate, filter and concentrate in vacuo to give a crude product. Purifiy via flash chromatography [5-10% CH3OH saturated with NH3 in CH2Cl2 ] to give the title compound, which can be triturated with isopropyl ether/pentane to give an off-white solid (249 mg, 85%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04804666 |
| Source dataset | uspto-grants-1989_02 |
| ORD ID | ord-3e75e386e6574c859b551290e1ebfca5 |
| Source note | uspto-grants-1989_02 |