1-Piperonylpiperazine → HCID 14303539, compound

HRID 476580Notes

Reaction equation

HRID 476580 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]1

Participants

4

Reactant 2

HCID 944261-PiperonylpiperazineHCID 19838008HCID 19838008, compound

Product 1

HCID 14303539HCID 14303539, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 9.4 g of 4-(3,4-methylenedioxybenzyl)piperazine in 100 ml of anhydrous 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 (3g) 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

  1. filtrationthe precipitate of amine hydrochloride is filtered off
  2. washwashed several times with benzene
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9aee54d81ad148afb4a317e6cd7b1b9c
Source dataset
uspto-grants-1989_12
Patent number
US04885299

Reaction notes

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