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4-Methylmorpholine → 2-Mesylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole

HRID 1649846
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1649846
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[N:6]=1.CN1CCOCC1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>CN(C)C=O.ClCCl>[S:36]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:10][CH2:9]2)[N:6]=1)([CH3:35])(=[O:38])=[O:37]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 198549372-Amino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole

Produkt 1

HCID 198549402-Mesylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazoleAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228Dimethylformamide
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred mixture of 2-amino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (0.78 g), N-methylmorpholine (1.15 ml) in N,N-dimethylformamide (8 ml) was added dropwise a solution of methanesulfonyl chloride (0.5 g) in dichloromethane (0.5 ml) under ice-bath cooling. After 1 hour, the reaction mixture was filtered. The filtrate was made basic with 1N sodium hydroxide solution (12 ml). After being stirred for 30 minutes, the mixture was neutralized with 1N hydrochloric acid and extracted with dichloromethane (40 ml×2). The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off and the residue was subjected to column chromatography on silica gel, and eluted with a mixture of chloroform and methanol (10:1 V/V). The fractions containing the object compound were combined and concentrated under reduced pressure to give white crystals. The crystals were recrystallized from ethanol to give 2-mesylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (0.32 g).

Aufarbeitung

  1. temperaturecooling
  2. filtrationthe reaction mixture was filtered
  3. extractionextracted with dichloromethane (40 ml×2)
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. washeluted with a mixture of chloroform and methanol (10:1 V/V)
  8. additionThe fractions containing the object compound
  9. concentrationconcentrated under reduced pressure
  10. customto give white crystals
  11. customThe crystals were recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-20abea351a314b408930ea4d8e02c440
Quelldatensatz
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04921887

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