N-Methylhomoveratrylamine → 7,7-Dimethyl-2-(4-chloro-phenyl)-5-[2-(N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino)-ethyl]-5H,7H-imidazo[4,5-h]-isoquinoline-4,6-dione dihydrochloride

HRID 47120

Reaktionsgleichung

Reaktionsgleichung von HRID 47120
[CH3:1][C:2]1([CH3:27])[C:11](=[O:12])[CH:10]2[C:5](=[C:6]3[N:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=4)[N:17]=[C:7]3[C:8](=[O:16])[CH:9]2[CH2:13][CH2:14][Cl:15])[CH:4]=[N:3]1.[CH3:28][NH:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH3:41])[CH:33]=1>C(Cl)(Cl)Cl>[ClH:15].[ClH:15].[CH3:27][C:2]1([CH3:1])[C:11](=[O:12])[CH:10]2[C:5](=[C:6]3[N:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=4)[N:17]=[C:7]3[C:8](=[O:16])[CH:9]2[CH2:13][CH2:14][N:29]([CH3:28])[CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH3:41])[CH:33]=2)[CH:4]=[N:3]1

Komponenten

4

Edukt 2

HCID 77039N-MethylhomoveratrylamineHCID 706104267,7-dimethyl-2-(4-chlorophenyl)-5-(2-chloro-ethyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione

Produkt 1

HCID 706110077,7-Dimethyl-2-(4-chloro-phenyl)-5-[2-(N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino)-ethyl]-5H,7H-imidazo[4,5-h]-isoquinoline-4,6-dione dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture consisting of 1.5 gm of 7,7-dimethyl-2-(4-chlorophenyl)-5-(2-chloro-ethyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione and 1.7 gm of N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amine was heated at 150° C. for 3 hours. After cooling the reaction mixture was dissolved in chloroform, and the solution was washed with water. The chloroform phase was evaporated, and the residue was chromatographed on a silicagel column (eluant: chloroform/acetone 19:1). The dihydrochloride was precipitated from acetone by addition of ethereal hydrochloric acid and recrystallized from methylene chloride/acetone.

Aufarbeitung

  1. temperatureAfter cooling the reaction mixture
  2. washthe solution was washed with water
  3. customThe chloroform phase was evaporated
  4. customthe residue was chromatographed on a silicagel column (eluant: chloroform/acetone 19:1)
  5. customThe dihydrochloride was precipitated from acetone by addition of ethereal hydrochloric acid
  6. customrecrystallized from methylene chloride/acetone

Quellen und Nachweise

ORD-Eintrag
ord-72fb132aac154e7b92d6bf9be397eb96
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04176184

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