Potassium Carbonate → N-(1-Fluorobenzyl)-N-indan-2-yl-2-(6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl]acetamide

HRID 916882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916882
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[CH:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:9][CH2:8][CH2:7]2.[F:22][C:23]1([CH:43]=[CH:42][CH:41]=[CH:40][CH2:39]1)[CH2:24][N:25]([CH:30]1[CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31]1)[C:26](=[O:29])[CH2:27]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:22][C:23]1([CH:39]=[CH:40][CH:41]=[CH:42][CH2:43]1)[CH2:24][N:25]([CH:30]1[CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31]1)[C:26](=[O:29])[CH2:27][C:10]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:5][C:4]([O:3][CH3:2])=[C:13]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:8][NH:9]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 126277306,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 69183190N-(1-fluorobenzyl)-N-indan-2-yl-2-bromoacetamide

Produkt 1

HCID 69494327N-(1-Fluorobenzyl)-N-indan-2-yl-2-(6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl]acetamideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (160, 153 mg, 0.5 mmol), N-(1-fluorobenzyl)-N-indan-2-yl-2-bromoacetamide (161, 180 mg, 0.5 mmol) and potassium carbonate (500 mg) in acetonitrile is heated at 80° C. overnight. After cooling, the mixture is filtered and concentrated. The resulting residue is purified by column chromatography eluting with 5% methanol in chloroform to provide the title product (162) as a thick oil (215 mg, 78%). 1H NMR (CDCl3) 6.8–7.3 (m, 14H), 6.60(s, 1H), 6.05 (s, 1H),

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered
  3. concentrationconcentrated
  4. customThe resulting residue is purified by column chromatography
  5. washeluting with 5% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-3aa6506ffe774da2a156d3c9687e50c1
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271270B2

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