Triethylamine → 2-(2',5'-Dimethoxybenzoyl)-1-methylene-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1647318

Reaktionsgleichung

Reaktionsgleichung von HRID 1647318
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:4]=1[C:5](Cl)=[O:6].[CH3:14][C:15]1[C:24]2[C:19](=[C:20]([O:29][CH3:30])[C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[CH2:18][CH2:17][N:16]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:4]=1[C:5]([N:16]1[CH2:17][CH2:18][C:19]2[C:24](=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[C:20]=2[O:29][CH3:30])[C:15]1=[CH2:14])=[O:6]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 873642,5-Dimethoxybenzoyl chlorideHCID 157445311-Methyl-5,6,7-trimethoxy-3,4-dihydroisoquinoline

Produkt 1

HCID 157445322-(2',5'-Dimethoxybenzoyl)-1-methylene-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinolineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

A solution of compound 45 (746 mg, 3.7 mmol) in anhydrous benzene (2 mL) was slowly added at room temperature to a solution of compound 44 (880 mg, 3.7 mmol) in anhydrous benzene (10 mL) containing triethylamine (568 mg, 5.6 mmol, 0.78 mL). The resulting solution was heated at reflux with stirring under Ar for 2 h. White NH4Cl precipitated and was removed by filtration. The filtrate was evaporated to dryness and the residue was subjected to flash chromatography (ether:triethylamine, 99:1 by volume, silica gel 230-300 mesh) to give compound 46 as an oil (1.3 g, 87.8%): 1H NMR (CDCl3, 200 MHz) δ6.87 (s, 1H), 6.85 (d, 1H, J=10 Hz), 6.80 (d, 1H, J=3 Hz), 6.70 (d, 1H, J=10 Hz), 5.21 (s, br 1H), 4.55 (s, br, 1H), 3.90 (s, 6H), 3.88 (s, 3H), 3.84 (s, 3H), 3.75 (s, 3H), 3.41 (s, br, 2H), 2.88 (t, 2H, J=6 Hz). CIMS (isobutane) m/e 400 (MH+, 100).

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux
  3. customWhite NH4Cl precipitated
  4. customwas removed by filtration
  5. customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-fa4823a31ad945249b1d55c50623e4e0
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05430062

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