Potassium Iodide → 7-methoxy-4-(1-methylethyl)-6-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-one

HRID 22331Notes

Reaction equation

HRID 22331 reaction equation
[OH:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]2[O:10][C:9](=[O:11])[CH:8]=[C:7]([CH:12]([CH3:14])[CH3:13])[C:6]=2[CH:15]=1.Cl[CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH3:17][O:16][C:3]1[C:2]([O:1][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:24][CH2:23]2)=[CH:15][C:6]2[C:7]([CH:12]([CH3:13])[CH3:14])=[CH:8][C:9](=[O:11])[O:10][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 139197Piperazine, 1-(3-chloropropyl)-4-phenyl-HCID 199276546-hydroxy-7-methoxy-4-(1-methylethyl)-2H-1-benzopyran-2-one

Product 1

HCID 199277237-methoxy-4-(1-methylethyl)-6-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-oneYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.0 g (17 mmol) 6-hydroxy-7-methoxy-4-(1-methylethyl)-2H-1-benzopyran-2-one (example 105), 4.7 g (20.5 mmol) 1-(3-chloropropyl)-4-phenylpiperazine, 4.7 g (34 mmol) potassium carbonate and 1.0 g potassium iodide are agitated in 300 ml DMF for 44 h under nitrogen at 60° C. After filtration and removal of the solvent in vacuum, the residue is taken up in chloroform and washed with dilute sodium hydroxide solution and with water, dried over sodium sulfate and then evaporated again. Yield 5.5 g (74%) of crystals with a fusion point of 94°-96° C. (from isopropanol and TBME). Fumarate: method E; yield 88%; fusion point 175°-176° C. (from isopropanol and ethanol).

Workup

  1. filtrationAfter filtration and removal of the solvent in vacuum
  2. washwashed with dilute sodium hydroxide solution and with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated again
  5. customwith a fusion point of 94°-96° C. (from isopropanol and TBME)
  6. customfusion point 175°-176° C. (from isopropanol and ethanol)

Sources & evidence

ORD record
ord-9cb8611447dc4306b5e24b475a7b5581
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Reaction notes

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