HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 3-{[(1-benzyl-3-methylpyrrolidin-3-yl)amino]methyl}-1-methylquinolin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 1-Methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde | HCID 4914628 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 1-Benzyl-3-methylpyrrolidin-3-amine | HCID 10511897 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-{[(1-benzyl-3-methylpyrrolidin-3-yl)amino]methyl}-1-methylquinolin-2(1H)-one | HCID 58415915 | — |
Reaction Steps
1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde (956 mg, 5.11 mmol), 1-benzyl-3-methylpyrrolidin-3-amine (972 mg, 5.11 mmol), and acetic acid (0.877 ml, 15.32 mmol) were combined in CH2Cl2 (25 ml) and stirred for 30 min. Sodium triacetoxyborohydride (3248 mg, 15.32 mmol) was added and the reaction stirred for 2.5 hours before being partitioned between CH2Cl2 and satd. bicarb. The aqueous portion was extracted 3×CH2Cl2, and the organic portion dried (Na2SO4) then concentrated in vacuo. The resulting material was carried on crude.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08389720B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-bd05b3504fec40c392b54907932d2357 |
| Source note | uspto-grants-2013_03 |