1-(3-Chlorophenyl)piperazine → 1-[4-(3-Chlorophenyl)piperazin-1-yl]-3-[2-oxopyrrolidin-1-yl]propane

HRID 1857950Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10].[Cl:11][C:12]1[CH:13]=[C:14]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:13]=[C:14]([N:18]2[CH2:23][CH2:22][N:21]([CH2:2][CH2:3][CH2:4][N:5]3[CH2:9][CH2:8][CH2:7][C:6]3=[O:10])[CH2:20][CH2:19]2)[CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1-chloro-3-[2-oxopyrrolidin-1-yl]propane (1.0 g, 6.2 mmol), 1-(3-chlorophenyl)piperazine (1.22 g, 6.2 minol), anhydrous Na2CO3 (0.33 g, 3.1 mmcl) and Nal (0.09~3 g, 0.6 mrnol) in dry toluene (10 ml) was stirred at 110° C. for 12 hrs. The solvent was removed at reduced pressure and residue was poured on water (20 ml). The separated residue was extracted with ethylacetate (3×20 ml), dried over Na2SO4 and concentrated under reduced pressure to give 1-[4-(3-chlorophenyl)piperazin-1-yl]-3-[2-oxopyrrolidin-1-yl]propane as an oil which was purified by flash column chromatography over silica gel using chloroform as eluent, yield 0.60 g (30.0%)

Workup

customThe solvent was removed at reduced pressure and residue
additionwas poured on water (20 ml)
extractionThe separated residue was extracted with ethylacetate (3×20 ml)
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e6fd0cf915804dc29601bb0e589d13c7
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150367

Reaction notes

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