Ammonium formate → 1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine

HRID 8723

Reaktionsgleichung

Reaktionsgleichung von HRID 8723
C([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([C:17]3[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=3)[CH:15]=[N:16][C:10]=2[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[C:19]1([CH3:23])[CH:20]=[CH:21][CH:22]=[C:17]([N:14]2[C:11]3[CH2:12][CH2:13][NH:8][CH2:9][C:10]=3[N:16]=[CH:15]2)[CH:18]=1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 219836255-benzyl-1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine

Produkt 1

HCID 219836441-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridineAusbeute 32,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 5-benzyl-1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine 17a (500 mg, 1.6 mmol), ammonium formate (1.0 g), and 700 mg 5% Pd/C (50% with water) in 80% aqueous methanol was heated at reflux for 12 hr, and then allowed to reach ambient temperature. The catalyst was removed by filtration through Celite®. The filtrate was evaporated in vacuo. Purification by silica gel chromatography provided 1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine (110 mg) 18a as an oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 12 hr
  3. customto reach ambient temperature
  4. customThe catalyst was removed by filtration through Celite®
  5. customThe filtrate was evaporated in vacuo
  6. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b8fb1c319e5948b89f7e69697197210e
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091200B2

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