Ethyl Acetate → 1-(7-Methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-3-chloropropane

HRID 1380861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1380861
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][C:8](=[O:12])[NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.[H-].[Na+].[Cl:17][CH2:18][CH2:19][CH2:20]I.C(OCC)(=O)C>CN(C)C(=O)N(C)C>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][C:8](=[O:12])[N:9]([CH2:20][CH2:19][CH2:18][Cl:17])[CH2:10][CH2:11][C:5]=2[CH:4]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 135206897-Methoxy-4,5-dihydro-1H-benzo[D]azepin-2(3H)-one

Produkt 1

HCID 135206901-(7-Methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-3-chloropropane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12437TetramethylureaLösungsmittel2×

Versuchsvorschrift

First, 7-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one (1.15 g, 6 mmol) is dissolved in absolute tetramethylurea (30 ml), mixed with 55% sodium hydride dispersion in oil (300 mg) and stirred for 2 hours at 20°-25° C. under a nitrogen atmosphere. The resulting reaction mixture is added dropwise, with stirring, at 15°-20° C. under a nitrogen atmosphere to 1-chloro-3-iodopropane (1.6 g, 7.8 mmol) dissolved in tetramethylurea (20 ml) and stirred for 3 hours at ambient temperature. Then, ethyl acetate (300 ml) are added and the mixture is extracted six times with water. The organic solution is dried over magnesium sulphate, concentrated by evaporation and the residue is purified oer a silica gel column with methylene chloride and increasing amounts of ethanol (up to 2%). Yield: 410 mg. IR spectrum (methylene chloride): 1650 cm-1 (C=O).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. additionis added dropwise
  3. stirringstirred for 3 hours at ambient temperature
  4. extractionthe mixture is extracted six times with water
  5. dry with materialThe organic solution is dried over magnesium sulphate
  6. concentrationconcentrated by evaporation
  7. customthe residue is purified oer a silica gel column with methylene chloride
  8. temperatureincreasing amounts of ethanol (up to 2%)

Quellen und Nachweise

ORD-Eintrag
ord-fce52bc5e8ee4708b9ae8212cf56dbf0
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04584293

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