Desipramine → {2-[3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propylamino]-ethyl]-carbamic Acid tert-butyl Ester

HRID 840511

Reaktionsgleichung

Reaktionsgleichung von HRID 840511
[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.C(=O)([O-])[O-].[K+].[K+].[C:27]([NH:34][CH2:35]CBr)([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].[I-].[Na+]>C1OCCOCCOCCOCCOCCOC1.CN(C)C=O.CC(C)=O>[C:30]([O:29][C:27](=[O:28])[NH:34][CH2:35][CH2:1][NH: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)([CH3:33])([CH3:32])[CH3:31]

Komponenten

8

Edukt 4

HCID 2995DesipramineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Produkt 1

HCID 86757926{2-[3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propylamino]-ethyl]-carbamic Acid tert-butyl EsterAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 2855718-Crown-6KatalysatorHCID 180AcetoneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 3.23 g (12.04 mmol) of desipramine free base was added 80 ml of dry acetone, 3.6 g of anhydrous potassium carbonate, 3.0 g (13.45 mmol) of 2-(BOC-amino) ethyl bromide, 3 ml of anhydrous dimethylformamide, 15 mg of 18-crown-6 and 500 mg of sodium iodide. The mixture was allowed to reflux 18 hours under argon atmosphere. The reaction mixture was cooled to room temperature and filtered. The residue was washed with 10 ml of acetone. The filtrate was concentrated and the residue was purified by silica gel column chromatography using 4% methanol in ethyl acetate to give 4.8 g (11.7 mmol, 96%) of 23 as a thick oil.

Aufarbeitung

  1. temperatureto reflux 18 hours under argon atmosphere
  2. filtrationfiltered
  3. washThe residue was washed with 10 ml of acetone
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-45a1cb867cff4c698d001297c3c0a26d
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06368814B1

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