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

HRID 1857949Notes

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.[Na+].[I-]>CN(C=O)C>[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: 70 °C

Procedure

A mixture of 1-chloro-3-[2-oxopyrrolidin-1-yl]propane (1 g, 6.2 mmol),, 1-(3-chlorophenyl)piperazine (1.22 g, 6.2 mmol) anhydrous Na2CO3 (0.33 g, 3.1 mmol) and NaI (0.093 g, 0.6 mmol) in dry DMF (5 ml) was stirred at 70° C. for 14 hrs. The reaction mixture was cooled, poured on water (20 ml) and the separated residue was extracted with CHCl3 (2×25 ml). The extracts were 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 1.50 g (75%). IR (Neat): 3020, 2820, 1660, 1590, 1450, 1210, 730. 1H NMR (CDCl3): 1.30-2.60(m, 12H, 3', 4', 2, 1 & 2×N-CH2), 2.40-3.50(m, 8H, 5', 3 & 2×N-CH2), 6.40-7.20(m, 4H, ArH). MS: m/z 321

Workup

temperatureThe reaction mixture was cooled
additionpoured on water (20 ml)
extractionthe separated residue was extracted with CHCl3 (2×25 ml)
dry with materialThe extracts were dried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-cca31b35849c42749dfd45caf740f02d
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150367

Reaction notes

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