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

HRID 1857951Notes

Reaction equation

HRID 1857951 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(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

6

Reactant 4

HCID 13551-(3-Chlorophenyl)piperazineHCID 10340Sodium CarbonateHCID 1859152-NaphthylalanineHCID 111056621-(3-Chloropropyl)pyrrolidin-2-one

Product 1

HCID 99271431-[4-(3-Chlorophenyl)piperazin-1-yl]-3-[2-oxopyrrolidin-1-yl]propane

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-chloro-3-[2-oxopyrrolidin-1-yl]propane (1 g, 6.2 mmcl), 1-(3-chlorophenyl)piperazine (1.22 g, 6.2 inmol) anhydrous Na2CO3 (0.33 g, 3.1 mmol) and Nal (0.093 g, 0.6 mmcl) in dry xylene (15 ml) was stirred at 150° C. for 14 hirs. The solvent was removed at reduced pressure and residue was poured on water (30 ml). The separated residue was extracted with dichloromethane (2×25 ml), dried over Na2SO4 and concentrated 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 fluent, yield 0.72 g (36%).

Workup

  1. customThe solvent was removed at reduced pressure and residue
  2. additionwas poured on water (30 ml)
  3. extractionThe separated residue was extracted with dichloromethane (2×25 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-181996a59ccf49ee832f2991d5d544ba
Source dataset
uspto-grants-2000_11
Patent number
US06150367

Reaction notes

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