Sodium Chloride → 1-[1-[1-(diphenylmethyl)azetidin-3-yl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

HRID 47532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47532
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[O:16])[CH2:3][CH2:2]1.[C:17]1([CH:23]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:24]2[CH2:27][CH2:26][C:25]2=O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+].[Cl-].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[C:17]1([CH:23]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:24]2[CH2:27][CH:26]([N:1]3[CH2:2][CH2:3][CH:4]([N:7]4[C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=5[NH:9][C:8]4=[O:16])[CH2:5][CH2:6]3)[CH2:25]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

8

Edukt 5

HCID 5234Sodium ChlorideHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 123767241-(Diphenylmethyl)azetidin-2-one

Produkt 1

HCID 227452971-[1-[1-(diphenylmethyl)azetidin-3-yl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-oneAusbeute 133,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

In 7 ml of methanol, 217 mg of 1-(piperidin-4-yl)-1,3-dihydro-2H-benzimidazol-2-one, 300 mg of 1-(diphenylmethyl)azetidin-2-one, 94 mg of sodium cyanoborohydride and 102 mg of zinc chloride were dissolved and stirred overnight. The reaction liquid was added to a saturated aqueous solution of sodium hydrogencarbonate to which sodium chloride had been added, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate and concentrated. Thus obtained residue was purified by silica gel column chromatography (chloroform, chloroform/methanol=50/1) to provide 583 mg of crude 1-[1-[1-(diphenylmethyl)azetidin-3-yl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one.

Aufarbeitung

  1. customThe reaction liquid
  2. additionhad been added
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThus obtained residue was purified by silica gel column chromatography (chloroform, chloroform/methanol=50/1)

Quellen und Nachweise

ORD-Eintrag
ord-072b9e6c020c4bfc94d9868adebbc4c0
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699880B1

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