1,1'-Carbonyldiimidazole → 2-oxo-3-(1-benzylpiperidin-4-yl)-2,3-dihydro-1H-imidazo[4,5-c]pyridine

HRID 271872

Reaktionsgleichung

Reaktionsgleichung von HRID 271872
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1.[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23]>O1CCCC1>[O:23]=[C:22]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:11][CH2:10]2)[C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:2]=2[NH:1]1

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 222932454-Amino-3-[(1-benzylpiperidin-4-yl)amino)pyridine

Produkt 1

HCID 222931702-oxo-3-(1-benzylpiperidin-4-yl)-2,3-dihydro-1H-imidazo[4,5-c]pyridineAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-amino-3-[(1-benzylpiperidin-4-yl)amino)pyridine (2.8 g, 9.9 mmol) and carbonyldiimidazole (3.0 g, 18.5 mmol) in tetrahydrofuran (100 mL) was refluxed overnight. The reaction was cooled, concentrated and partitioned between chloroform (500 mL) and saturated sodium carbonate (100 mL). The organic phase was dried over magnesium sulfate and concentrated to give the title compound (2.8 g). MS 209 (M+1).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. custompartitioned between chloroform (500 mL) and saturated sodium carbonate (100 mL)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-93308ea79f34403e871e5a458a6d6141
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452903B2

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