Sodium Iodide → 1-[4-(4-Ethylphenyl)piperazin-1-yl]-3-[2-oxopyrrolidin-1-yl]propane

HRID 1857952Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-chloro-3-[2-oxopyrrolidin-1-yl]propane (2.0 g, 12.0 mmol), 1-(4-ethylphenyl)piperazine (2.36 g, 12.0 mmol), anhydrous Na2CO3 (0.658 g, 6.2 mmol) and NaI (0.18 g, 1.2 mmol) in dry DMF (10 ml) was stirred at 80° C. for 12 hrs. The reaction mixture was cooled, poured on water (30 ml) and the separated residue was extracted with CHCl3 (2×30 ml). The extracts were dried over Na2So4 and concentrated under reduced pressure to give 1-[4-(4-ethylphenyl)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 2.43 g (62.0%). IR (Neat): 2940, 2800, 1660, 1440, 1000, 900,800. 1H NMR (CDCl3): 1.20(t, 3H, J=6.0 Hz, CH2CH3, 1.60-280(m, 14H, 3',4',2,1 & 2×N--CH2, CH2CH3), 3.00-3.60(m, 8H, 5', 3 & 2×N--CH2). MS: m/z 315 (M+).

Workup

temperatureThe reaction mixture was cooled
additionpoured on water (30 ml)
extractionthe separated residue was extracted with CHCl3 (2×30 ml)
customThe extracts were dried over Na2So4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ac18d3ec333a41908c983aabe6172a3a
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150367

Reaction notes

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