1-(2-Methoxyphenyl)piperazine → HCID 18544411, compound

HRID 1268378Notes

Reaction equation

HRID 1268378 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.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.COCCOC>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH:10]([CH2:13][N:26]3[CH2:25][CH2:24][N:23]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[O:16][CH3:15])[CH2:28][CH2:27]3)[C:9]2=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 80711,2-DimethoxyethaneHCID 3219041-(4-bromophenyl)-3-methylene-2-pyrrolidinone

Product 1

HCID 18544411HCID 18544411, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.31 g of 1-(4-bromophenyl)-3-methylene-2-pyrrolidinone and 2.00 g of 4-(2-methoxyphenyl)piperazine were mixed with 5 ml of ethylene glycol dimethyl ether. The mixture was refluxed for 2 hours 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 then concentrated to obtain an oily material. The oily material was purified by silica gel column chromatography using a mixed solvent of chloroform/methanol=40/1 to obtain 1.88 g of oily 1-(4-bromophenyl)-3-[4-(2-methoxyphenyl)piperazine-1-yl]methyl-2-pyrrolidinone.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  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. customto obtain an oily material
  7. customThe oily material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5faf62f0f7b342d9a855d86368fc218f
Source dataset
uspto-grants-2003_04
Patent number
US06555694B1

Reaction notes

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