Dimethylamine → 8-(2-Chlorobenzyloxy)-3-dimethylaminomethyl-2-methylimidazo[1,2-a]pyridine

HRID 4297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 4297
[CH2:1]=O.[CH3:3][NH:4][CH3:5].[Cl:6][C:7]1[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=1[CH2:9][O:10][C:11]1[C:12]2[N:13]([CH:17]=[C:18]([CH3:20])[N:19]=2)[CH:14]=[CH:15][CH:16]=1>C(O)(=O)C>[Cl:6][C:7]1[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=1[CH2:9][O:10][C:11]1[C:12]2[N:13]([C:17]([CH2:3][N:4]([CH3:1])[CH3:5])=[C:18]([CH3:20])[N:19]=2)[CH:14]=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 138259328-(2-Chlorobenzyloxy)-2-methylimidazo[1,2-a]pyridine

Produkt 1

HCID 138259368-(2-Chlorobenzyloxy)-3-dimethylaminomethyl-2-methylimidazo[1,2-a]pyridineAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 37% aqueous formaldehyde (2.38 g) in acetic acid (38 ml) was added dropwise 50% aqueous dimethylamine (2.63 g) with ice-cooling over a period of 10 minutes and the mixture was stirred for an additional 10 minutes. The mixture was heated at 50°-55° C. for 2 hours after an addition of 8-(2-chlorobenzyloxy)-2-methylimidazo[1,2-a]pyridine (7.6 g) thereto and then evaporated in vacuo. The residue was basified with aqueous sodium hydroxide and extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residual solid was recrystallized from a mixture of diethyl ether and n-hexane to give 8-(2-chlorobenzyloxy)-3-dimethylaminomethyl-2-methylimidazo[1,2-a]pyridine (7.85 g).

Aufarbeitung

  1. temperaturecooling over a period of 10 minutes
  2. temperatureThe mixture was heated at 50°-55° C. for 2 hours
  3. customevaporated in vacuo
  4. extractionextracted with methylene chloride
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residual solid was recrystallized from a mixture of diethyl ether and n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-92e60f8984b44a1db9d8ae0442b210af
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725601

Notizen zur Reaktion

Wird geladen…