Ammonia methanol → Benzyl cis(+/-)-(1-carbamothioyl-3-methoxypiperidin-4-yl)-carbamate

HRID 43513

Reaktionsgleichung

Reaktionsgleichung von HRID 43513
[N:1]1([C:6]([N:8]2[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@H:10]([O:25][CH3:26])[CH2:9]2)=[S:7])C=CN=C1.N.CO>C1COCC1.[Cl-].[Na+].O>[C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:10]([O:25][CH3:26])[CH2:9]1)(=[S:7])[NH2:1]

Komponenten

5

Edukt 2

HCID 21705897Ammonia methanolHCID 86648520Benzyl cis(+/-)-[1-(1H-imidazol-1-ylcarbonothioyl)-3-methoxypiperidin-4-yl]-carbamate

Produkt 1

HCID 86648521Benzyl cis(+/-)-(1-carbamothioyl-3-methoxypiperidin-4-yl)-carbamateAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Benzyl cis(±)-[1-(1H-imidazol-1-ylthiocarbonyl)-3-methoxypiperidin-4-yl]-carbamate obtained in Example (64a) (about 1.36 mmol) was dissolved in THF (2 mL). A 2 N ammonia/methanol solution (10 mL) was added, and the mixture was stirred for 42 hours. Brine was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The precipitated solid was collected by filtration to obtain 296.5 mg of the title compound as a white solid (67%).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe precipitated solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-413e645128ff40229443a53d13eb9b8f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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