Sodium Bicarbonate → 2-Propionylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole

HRID 1649844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1649844
Cl[CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:12])[CH2:10][CH3:11])[S:6][CH:7]=1.[C:13]1([CH:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:9]([NH:8][C:5]1[S:6][CH:7]=[C:3]([CH2:2][N:24]2[CH2:25][CH2:26][CH:21]([O:20][CH:19]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:22][CH2:23]2)[N:4]=1)(=[O:12])[CH2:10][CH3:11]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 30175844-BenzhydryloxypiperidineHCID 103980162-Propionylamino-4-chloromethylthiazole

Produkt 1

HCID 145008962-Propionylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazoleAusbeute 26,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred mixture of 4-chloromethyl-2-propionylaminothiazole (0.64 g), 4-(diphenylmethoxy)piperidine (0.8 g) and sodium bicarbonate (0.3 g) in N,N-dimethylformamide (8 ml) was heated at 80° to 90° C. for 2 hours. The reaction mixture was poured into ice water. The resulting precipitate was collected, washed with water and dried in vacuo. The precipitate 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. The residue was triturated with diisopropyl ether to give white crystals. The crystals were recrystallized from a mixture of toluene and diisopropyl ether and dried under reduced pressure to give 2-propionylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (0.35 g).

Aufarbeitung

  1. temperaturewas heated at 80° to 90° C. for 2 hours
  2. customThe resulting precipitate was collected
  3. washwashed with water
  4. customdried in vacuo
  5. washeluted with a mixture of chloroform and methanol (10:1 V/V)
  6. additionThe fractions containing the object compound
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with diisopropyl ether
  9. customto give white crystals
  10. customThe crystals were recrystallized from a mixture of toluene and diisopropyl ether
  11. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1fdb981b6a1a48e49956a79e025dd182
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04921887

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