1-Piperonylpiperazine → HCID 14303539, compound
Reaction equation
[CH2:1]1[O:16][C:15]2[CH:14]=[CH:13][C:5]([CH2:6][N:7]3[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]3)=[CH:4][C:3]=2[O:2]1.[O:17]=[C:18]1[CH:22]([CH2:23][C:24]([Cl:26])=[O:25])[C:21]2[CH:27]=[CH:28][CH:29]=[CH:30][C:20]=2[O:19]1>C1C=CC=CC=1>[ClH:26].[O:17]=[C:18]1[CH:22]([CH2:23][C:24]([N:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:13]=[CH:14][C:15]4[O:16][CH2:1][O:2][C:3]=4[CH:4]=3)[CH2:8][CH2:9]2)=[O:25])[C:21]2[CH:27]=[CH:28][CH:29]=[CH:30][C:20]=2[O:19]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 9.4 g of 4-(3,4-methylenedioxybenzyl)piperazine in 100 ml of anyhydrous benzene is added to a solution, cooled beforehand to 10° C., of 4.5 g of 2-(2,3-dihydro-2-oxo-3-benzofuranyl)acetyl chloride in 50 ml of anhydrous benzene. The mixture is stirred for 12 hours at room temperature and the precipitate of amine hydrochloride is filtered off and washed several times with benzene. The combined organic phases are washed with water, dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product obtained is chromatographed on 300 g of 70-230 mesh silica (eluant: dichloromethane/methanol 9.5:2.5 V/V). The resulting product (3 g) is dissolved in the minimum amount of acetone and crystallized in the form of the hydrochloride by adding 1.5 ml of 5.07N ethanolic hydrochloric acid.
Workup
- filtrationthe precipitate of amine hydrochloride is filtered off
- washwashed several times with benzene
- washThe combined organic phases are washed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-f82fc3b0708346a7964be45d317d3946
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04859700
Reaction notes
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