1-(2-Methoxyphenyl)piperazine → HCID 24835288, compound

HRID 1452323Notes

Reaction equation

HRID 1452323 reaction equation
[CH3:1][N:2]([CH2:23][CH2:24][Cl:25])[C:3]([C:5]1[C:14]2[O:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([CH3:21])[C:10](=[O:22])[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[ClH:25].[CH3:1][N:2]([CH2:23][CH2:24][N:37]1[CH2:36][CH2:35][N:34]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[O:27][CH3:26])[CH2:39][CH2:38]1)[C:3]([C:5]1[C:14]2[O:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([CH3:21])[C:10](=[O:22])[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 19972458HCID 19972458, compound

Product 1

HCID 24835288HCID 24835288, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3.56 g of Intermediate XV, 2.35 g of 1-(2-methoxyphenyl)-piperazine, 2.76 g of anhydrous potassium carbonate and 1.66 g of potassium iodide in 25 ml of dimethylformamide was stirred at 100° C. for 6 hours. After cooling, the solvent was removed in vacuo and the residue was taken up in 50 ml of water, stirred for 1 hour at room temperature, collected by filtration, washed with water and crystallized from 95% ethanol in the presence of a small amount of activated charcoal (for decoloring). The base was dissolved in 105 ml of boiling 0.086N aqueous hydrochloric acid solution. After cooling, the crystallized salt was collected by filtration, giving 4.3 g of the title compound (m.p. 201°-203° C.).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuo
  3. stirringstirred for 1 hour at room temperature
  4. filtrationcollected by filtration
  5. washwashed with water
  6. customcrystallized from 95% ethanol in the presence of a small amount of activated charcoal (for decoloring)
  7. dissolutionThe base was dissolved in 105 ml
  8. temperatureAfter cooling
  9. filtrationthe crystallized salt was collected by filtration

Sources & evidence

ORD record
ord-48394c5d676d4339bf3e27e63f9fd4cc
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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