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Triethylamine → 1-[1-(1-(tert-butoxycarbonyl)piperidin-4-yl)piperidin-4-yl]-3-(methylsulfonyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 47535
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 47535
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[NH:22][C:21]3=[O:29])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:15][CH2:16][CH:17]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[N:22]([S:38]([CH3:37])(=[O:40])=[O:39])[C:21]3=[O:29])[CH2:18][CH2:19]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 15839551HCID 15839551, Verbindung

Produkt 1

HCID 227453061-[1-(1-(tert-butoxycarbonyl)piperidin-4-yl)piperidin-4-yl]-3-(methylsulfonyl)-1,3-dihydro-2H-benzimidazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212
Chloroform
Lösungsmittel

Versuchsvorschrift

One (1) g of 1-[1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one (cf. International Publication WO 96/13262) and 0.53 ml of triethylamine were suspended in 30 ml of chloroform. To the suspension 0.29 ml of methanesulfonyl chloride was added, followed by 2 hours' stirring at room temperature. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction liquid, which was then extracted with chloroform. The extract was dried over sodium sulfate, concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform, chloroform/methanol=19/1) to give 860 mg of 1-[1-(1-(tert-butoxycarbonyl)piperidin-4-yl)piperidin-4-yl]-3-(methylsulfonyl)-1,3-dihydro-2H-benzimidazol-2-one. The product was dissolved in 25 ml of trifluoroacetic acid, stirred for 30 minutes at room temperature and then the trifluoroacetic acid was distilled off. To the residue ether and chloroform were added and whereby obtained crystals were recovered by filtration, to give 860 mg of the title compound.

Aufarbeitung

  1. extractionwas then extracted with chloroform
  2. dry with materialThe extract was dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe resulting residue was purified by silica gel column chromatography (chloroform, chloroform/methanol=19/1)

Quellen und Nachweise

ORD-Eintrag
ord-091081c242494cbcb6af9e3eeff35824
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06699880B1

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