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

HRID 840511

Reaction equation

HRID 840511 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

HCID 86757926{2-[3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propylamino]-ethyl]-carbamic Acid tert-butyl EsterYield 97.2%

Reagents, catalysts & solvents 3

HCID 2855718-Crown-6CatalystHCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-45a1cb867cff4c698d001297c3c0a26d
Source dataset
uspto-grants-2002_04
Patent number
US06368814B1

Linked notes

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