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1-(2-Methoxyphenyl)piperazine → HCID 19972378, compound

HRID 2259910
Notes
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Reaction equation

HRID 2259910 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5][C:6]1[C:15]2[O:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([CH3:22])[C:11](=[O:23])[C:10]=2[CH:9]=[CH:8][CH:7]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][CH2:36][N:35]([CH2:2][CH2:3][CH2:4][S:5][C:6]2[C:15]3[O:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[C:12]([CH3:22])[C:11](=[O:23])[C:10]=3[CH:9]=[CH:8][CH:7]=2)[CH2:34][CH2:33]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 19972791HCID 19972791, compound

Product 1

HCID 19972378HCID 19972378, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4.4 g of Intermediate XXXIV, 2.5 g of 1-(2-methoxyphenyl)-piperazine, 1 g of potassium iodide and 1.8 g of anhydrous potassium carbonate in 40 ml of dimethylformamide was stirred at 100° C. for 3 hours. After cooling to 20°-25° C., the reaction mixture was poured into 350 ml of water and extracted with dichloromethane. The organic extracts were washed with water and dried on anhydrous sodium sulfate, and the solvent was then evaporated off in vacuo. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate:petroleum ether 3:2, and by crystallization from ethanol, yielding 3.9 g of the title compound, m.p. (70) 96°-99° C.

Workup

  1. temperatureAfter cooling to 20°-25° C.
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customthe solvent was then evaporated off in vacuo
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with ethyl acetate:petroleum ether 3:2
  8. customby crystallization from ethanol

Sources & evidence

ORD record
ord-d00094f6c66e4a0eaa4ba0e337492969
Source dataset
uspto-grants-1995_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05474994

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes