Potassium Carbonate → [3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-carbamic acid octyl ester

HRID 416466

Reaktionsgleichung

Reaktionsgleichung von HRID 416466
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][N:6]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][CH2:13][C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]1=2.Cl.[C:22](=[O:25])([O-])[O-:23].[K+].[K+].[CH2:28]([C:36](Cl)(Cl)Cl)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]C>CN(C=O)C>[CH2:36]([O:23][C:22](=[O:25])[N:2]([CH2:3][CH2:4][CH2:5][N:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=2)[CH3:1])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 65327Desipramine HydrochlorideHCID 64203871,1,1-Trichlorononane

Produkt 1

HCID 58600259[3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-methyl-carbamic acid octyl esterAusbeute 28,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Desipramine hydrochloride (1 equivalent, 0.3 gram) was added drop wise to a stirred solution of potassium carbonate (2.5 equivalents, 0.34 gram) in dry DMF at 0° C. Octyl chloroform (1.5 equivalents, 0.429 grams) which had been dissolved in dry DMF was added drop wise to this mixture and stirred for 12 hours at room temperature. The reaction mixture was quenched with water, extracted with ethyl acetate, the organic layer separated, washed with brine solution and dried over anhydrous sodium sulfate. The dried material was concentrated and purified by column chromatography to provide a pale yellow liquid (yield: 0.12 gram) and analyzed by HPLC (purity 95.3%) The FTIR, MS and 1H NMR spectra were consistent with the assigned structure with the empirical formula of C27H38N2O2.

Aufarbeitung

  1. additionwas added drop wise to this mixture
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customthe organic layer separated
  5. washwashed with brine solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe dried material was concentrated
  8. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d442b638dcd0440ca1881b8190ac9bab
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088918B2

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