Pyridine → Ammonia methanol

HRID 637013

Reaktionsgleichung

Reaktionsgleichung von HRID 637013
Cl[C:2]1[N:6]([CH2:7][CH2:8][O:9][CH2:10][CH3:11])[C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[N:3]=1.[NH:16]1[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.N12CCCN=C1CCCCC2.N1C=CC=CC=1>CO.C(OCC)(=O)C>[NH3:3].[CH3:8][OH:9].[CH2:10]([O:9][CH2:8][CH2:7][N:6]1[C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[N:3]=[C:2]1[N:16]1[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH3:11]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 68163Hexahydro-1,4-diazepineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 104893562-chloro-1-(2-ethoxyethyl)-1H-benzimidazole

Produkt 2

HCID 9984168Emedastine EP Impurity EHCID 21705897Ammonia methanolAusbeute 2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

Combine 2-chloro-1-(2-ethoxyethyl)-1H-benzimidazole (12.2 g, 54.2 mmol) and [1,4]diazepane (11.34 g, 113 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (9 mL), and pyridine (90 mL). Heat to reflux. After 18 hours, cool to ambient temperature and evaporate in vacuo to give a residue. Partition the residue between aqueous 1 M sodium hydroxide solution and ethyl acetate. Separate the layers and extract the aqueous layer two times with ethyl acetate. Combine the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 30% methanol/ethyl acetate and then 2% concentrated aqueous ammonia/methanol to give the title compound: Rf=0.26 (silica gel, 2% concentrated aqueous ammonia/methanol).

Aufarbeitung

  1. temperatureHeat to reflux
  2. customevaporate in vacuo
  3. customto give a residue
  4. customPartition the residue between aqueous 1 M sodium hydroxide solution and ethyl acetate
  5. customSeparate the layers
  6. extractionextract the aqueous layer two times with ethyl acetate
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-6d470da4b5db4bd28db13aa7913d5c2b
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194406B1

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