2,6-Piperidinedione, 3-[5-(aminomethyl)-1,3-dihydro-1-oxo-2H-isoindol-2-yl]- synthesis
- Product Name:2,6-Piperidinedione, 3-[5-(aminomethyl)-1,3-dihydro-1-oxo-2H-isoindol-2-yl]-
- CAS Number:1010100-28-3
- Molecular formula:C14H15N3O3
- Molecular Weight:273.29
1010100-27-2
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Yield: 40%
Reaction Conditions:
with methanesulfonic acid;palladium 10% on activated carbon;hydrogen in N,N-dimethyl acetamide at 40; under 2585.81 Torr; for 20 h;
Steps:
1.6.E E. 3-(5-(aminomethyl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione:
2-(2,6- Dioxopiperidin-3-yl)-1-oxoisoindoline-5-carbonitrile (10 g, 37.13 mmol), methanesulfonic acid (2.6 mL, 40.85 mmol), 10% dry Palladium on carbon (4 g) and dimethylacetamide (320 mL) were combined and shaken in a hydrogenation vessel and kept under 50 Psi at 40 °C for 20 h. The hydrogen atmosphere was evacuated and the mixture was filtered through a celite pad, washed with water (100 mL), and concentrated. To the resulting residue was added 1% methanol-dichloromethane which upon filtration and drying under high vacuum gave 3-(5- (aminomethyl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (5.6 g, 15.17 mmol, 40% yield) as an off-white solid. MS (ESI) m/z 272.0 [M-1].
References:
CELGENE CORPORATION;FILVAROFF, Ellen;LOPEZ-GIRONA, Antonia;LU, Gang WO2017/120446, 2017, A1 Location in patent:Paragraph 00468
1010100-26-1
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99548-55-7
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