Water → HCID 20150399, compound

HRID 568733Notes

Reaction equation

HRID 568733 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]1[C:10]([CH3:36])=[C:11]([CH3:35])[C:12]2[O:17][C:16]([CH2:19][CH2:20][CH2:21]OS(C3C=CC(C)=CC=3)(=O)=O)([CH3:18])[CH2:15][CH2:14][C:13]=2[C:33]=1[CH3:34].O>C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[C:10]([CH3:36])=[C:11]([CH3:35])[C:12]2[O:17][C:16]([CH2:19][CH2:20][CH2:21][N:1]3[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)([CH3:18])[CH2:15][CH2:14][C:13]=2[C:33]=1[CH3:34]

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 20150417HCID 20150417, compound

Product 1

HCID 20150399HCID 20150399, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a refluxing solution of 7.2 g (0.085 mol) of piperazine in 50 ml of toluene was added 3.8 g (8.5 mmol) of the 3,4-dihydro-6-methoxy-2-[3-(p-toluenesulfonyloxy)propyl]-2,5,7,8-tetramethyl-2H-benzopyran obtained in the above manner, followed by refluxing for 6 hours. After cooling, the reaction mixture was poured into water and extracted with diethyl ether. The ether layer was dried over anhydrous sodium sulfate and low-boiling substances were distilled off therefrom under reduced pressure and the excess piperazine was then removed by sublimation under reduced pressure. The thus-obtained residue was purified by silica gel column chromatography to give 2.7 g (91.8% yield) of 3,4-dihydro-6-methoxy-2-[3-(piperazin-1-yl)propyl]-2,5,7,8-tetramethyl-2H-benzopyran.

Workup

  1. customobtained in the above manner
  2. temperatureby refluxing for 6 hours
  3. temperatureAfter cooling
  4. extractionextracted with diethyl ether
  5. dry with materialThe ether layer was dried over anhydrous sodium sulfate and low-boiling substances
  6. distillationwere distilled off
  7. customunder reduced pressure and the excess piperazine was then removed by sublimation under reduced pressure
  8. customThe thus-obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bb47a8c12e9841d2af350c9a5ca51260
Source dataset
uspto-grants-1988_03
Patent number
US04728650

Reaction notes

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