1-(2-Methoxyphenyl)piperazine → HCID 18544409, compound

HRID 1268379Notes

Reaction equation

HRID 1268379 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][C:10](=[CH2:13])[C:9]2=[O:14])=[CH:4][CH:3]=1.COC1C=CC=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27]NCC1.N1CCCC1>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH:10]([CH2:13][N:23]3[CH2:18][CH2:19][CH2:27][CH2:28]3)[C:9]2=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 31268PyrrolidineHCID 3219041-(4-bromophenyl)-3-methylene-2-pyrrolidinone

Product 1

HCID 18544409HCID 18544409, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

There were mixed 1.31 g of 1-(4-bromophenyl)-3-methylene-2-pyrrolidinone, 2.00 g of 4-(2-methoxyphenyl)piperazine and 5 ml of pyrrolidine. The mixture was refluxed for 1 hour and then cooled. Thereto was added water. The mixture was subjected to extraction with ethyl acetate twice. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of chloroform/methanol=40/1 to obtain 1.79 g of 1-(4-bromophenyl)-3-pyrrolidinomethyl-2-pyrrolidinone.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. temperaturecooled
  3. extractionThe mixture was subjected to extraction with ethyl acetate twice
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2fde3bed95f047eba4f71adec0c8375c
Source dataset
uspto-grants-2003_04
Patent number
US06555694B1

Reaction notes

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