Potassium Carbonate → 2,5-Pyrrolidinedione, 1-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]-

HRID 2229801Notes

Reaction equation

[O:1]=[C:2]1[CH2:6][CH2:5][C:4](=[O:7])[NH:3]1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24]Cl)[CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][CH2:24][N:3]2[C:4](=[O:7])[CH2:5][CH2:6][C:2]2=[O:1])[CH2:20][CH2:21]1

Participants

Conditions

Temperature: 80 °C

Procedure

Scheme-I: A mixture of 2,5-dioxopyrrolidine (3.68 g, 37.24 mmol), 1-[4-(2-methoxyphenyl)-piperazin-1-yl]-3-chloropropane (10.0 g, 37.24 mmol), potassium carbonate (7.70 g, 55.8 mmol) and tetrabutylammonium bromide (2.38 g, 7.4 mmol) in acetone (100 ml) was refluxed for 12 hours at 80° C. with stirring. The solvent was evaporated off in vacuo and the residue was taken up in water (80 ml). The aqueous solution was extracted with chloroform (3×50 ml) and the organic layers combined, washed with water (2×50 ml); dried over Na2SO4 and evaporated in vacuo to give the title compound. The product was purified by column chromatography over flash silica gel using chloroform-methanol (99:1) as eluent; yield 8.00 g (65%) in oil. The hydrochloride salt was prepared by the method described above; mp 199-202° C.

Workup

customThe solvent was evaporated off in vacuo
extractionThe aqueous solution was extracted with chloroform (3×50 ml)
washwashed with water (2×50 ml)
dry with materialdried over Na2SO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-b17891d1bb4e4b2aa467c1957a317127
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420559B1

Reaction notes

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