1-(2-Methoxyphenyl)piperazine → HCID 19972545, compound

HRID 2259906Notes

Reaction equation

HRID 2259906 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][CH2:5][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>[ClH:1].[ClH: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][N:35]([CH2:2][CH2:3][O:4][CH2:5][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

Participants

7

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 19972767HCID 19972767, compound

Product 1

HCID 19972545HCID 19972545, compoundYield 153.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4 g of Intermediate XVIII, 2.4 g of 1-(2-methoxyphenyl)-piperazine, 1.96 g of potassium iodide and 1.65 g of anhydrous potassium carbonate in 40 ml of anhydrous dimethylformamide was stirred at 90° C. for 7 hours. After cooling to ambient temperature, the mixture was poured into water and extracted with dichloromethane. The combined extracts were washed with aqueous sodium chloride solution, dried on anhydrous sodium sulfate and evaporated to dryness in vacuo. The residue was crystallized from ethyl acetate and the collected crystals were dissolved in ethanol and treated with excess ethanolic hydrogen chloride to give 5.21 g of the title compound, m.p. 199-°201! C.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with dichloromethane
  3. washThe combined extracts were washed with aqueous sodium chloride solution
  4. dry with materialdried on anhydrous sodium sulfate
  5. customevaporated to dryness in vacuo
  6. customThe residue was crystallized from ethyl acetate
  7. dissolutionthe collected crystals were dissolved in ethanol
  8. additiontreated with excess ethanolic hydrogen chloride

Sources & evidence

ORD record
ord-cf05f38d25bf4c8a9de2df46c7824276
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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