1-(2-Methoxyphenyl)piperazine → HCID 54066594, compound

HRID 1653803Notes

Reaction equation

HRID 1653803 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]1[O:9][CH2:8][CH2:7][O:6]1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>CN(C)C=O>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH2:23][CH2:22][N:21]([CH2:2][CH2:3][CH2:4][CH:5]2[O:9][CH2:8][CH2:7][O:6]2)[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5520722-(3-Chloropropyl)-1,3-dioxolane

Product 1

HCID 54066594HCID 54066594, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.4 g of 2-(3-chloropropyl)-dioxolan and 15.9 g of 1-(2-methoxyphenyl)-piperazine in 60 ml of dimethylformamide was stirred at 80° C. for 4 hours. After cooling to 20°-25° C., the reaction mixture was poured into 500 ml of ice cold 0.5N sodium hydroxide solution and extracted with dichloromethane. The organic phase was washed with water and dried on anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel, eluting with dichloromethane:ethanol 95:5. 9.8 g of 2-{3-[4-(2-methoxyphenyl)-1-piperazinyl]-propyl}-dioxolan was obtained as an oil.

Workup

  1. temperatureAfter cooling to 20°-25° C.
  2. extractionextracted with dichloromethane
  3. washThe organic phase was washed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash chromatography on silica gel
  7. washeluting with dichloromethane:ethanol 95:5

Sources & evidence

ORD record
ord-872adb6875554970a602897bdf6dab01
Source dataset
uspto-grants-1995_04
Patent number
US05403842

Reaction notes

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