4-Piperidinecarboxamide → 1-(Naphthylsulfonyl)piperidine-4-carboxamide
Reaktionsgleichung
[NH2:1][C:2]([CH:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)=[O:3].C(N(CC)CC)C.[C:17]1([S:27](Cl)(=[O:29])=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1>O1CCCC1>[NH2:1][C:2]([CH:4]1[CH2:9][CH2:8][N:7]([S:27]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)(=[O:29])=[O:28])[CH2:6][CH2:5]1)=[O:3]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a suspension of 4-aminocarbonylpiperidine (12.8 g, 100 mmol) in dry tetrahydrofuran (250 μL) containing triethylamine (20.2 g, 200 mmol) stirring at room temperature under argon, was added 1-naphthalenesulfonyl chloride (25 g, 110 mmol). After 16 h the solvent was evaporated under vacuum, and a solution of 25% methanol in diethyl ether (250 mL) was added to the residue. The resulting mixture was stirred for 2 h before the solid was filtered. The solid was washed with diethyl ether (50 mL twice), then water (50 mL twice), followed by diethyl ether (50 mL twice) again before drying under vacuum. This provided 4-aminocarbonyl-1-(1-naphthylsulfonyl)piperidine (27.9 g, 88% yield) as a white solid.
Aufarbeitung
- customAfter 16 h the solvent was evaporated under vacuum
- additiona solution of 25% methanol in diethyl ether (250 mL) was added to the residue
- stirringThe resulting mixture was stirred for 2 h before the solid
- filtrationwas filtered
- washThe solid was washed with diethyl ether (50 mL twice), then water (50 mL twice),
- custombefore drying under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-eca539380f3040539aafb91819d1a434
- Quelldatensatz
- uspto-grants-2009_04
- Patentnummer
- US07517991B2
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