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.Cl.[C:22](=[O:25])([O-])[O-:23].[K+].[K+].[CH2:28](C(Cl)(Cl)Cl)[CH:29]([CH3:31])[CH3:30]>CN(C=O)C>[CH2:28]([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])[CH:29]([CH3:31])[CH3:30]Participants
Procedure
Desipramine hydrochloride (1 equivalent, 0.3 gram) was added drop wise to a stirred solution of potassium carbonate (5 equivalents, 0.68 gram) in dry DMF at 0° C. Isobutyl chloroform (1.5 equivalents, 0.18 ml) which had been dissolved in dry DMF was added drop wise to this mixture and stirred for 6 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: 0.18 gram) and analyzed by HPLC (purity 96.4%) The FTIR, MS and 1H NMR spectra were consistent with the assigned structure with the empirical formula of C22H28N2O2.
Workup
- additionwas added drop wise to this mixture
- customThe reaction mixture was quenched with water
- extractionextracted with ethyl acetate
- customthe organic layer separated
- washwashed with brine solution
- dry with materialdried over anhydrous sodium sulfate
- concentrationThe dried material was concentrated
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-0982d07644024c5da299cb9893bf33bd
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088918B2
Linked notes
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