Acetonitrile → [4-(2-Methoxy-ethyl)-piperazin-1-yl]-benzoic acid methyl ester

HRID 478636Notes

Reaction equation

HRID 478636 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.Br[CH2:18][CH2:19][O:20][CH3:21].[C:22](=[O:25])([O-])[O-:23].[K+].[K+].[C:28](#N)C>>[CH3:28][O:23][C:22](=[O:25])[C:6]1[CH:5]=[CH:4][CH:9]=[CH:8][C:7]=1[N:10]1[CH2:11][CH2:12][N:13]([CH2:18][CH2:19][O:20][CH3:21])[CH2:14][CH2:15]1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 15429161Methyl 4-(piperazin-1-yl)benzoate

Product 1

HCID 69996255[4-(2-Methoxy-ethyl)-piperazin-1-yl]-benzoic acid methyl ester

Conditions

Temperature
80 °C

Procedure

4-(Piperazin-1-yl)-benzoic acid methyl ester (19 mmol), 2-bromoethylmethylether (21 mmol), and potassium carbonate (22.8 mmol) are suspended in acetonitrile (50 ml) and stirred at 80° C. for 8 hours. After evaporation of the solvent, the residue is dissolved in water and extracted three times with CH2Cl2. The extract is dried over sodium sulfate and evaporated. The residue is suspended in diethylether/pentane and the solid filtered of and dried (vacuum). A powder with mp. 103-105° C. is obtained.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue is dissolved in water
  3. extractionextracted three times with CH2Cl2
  4. dry with materialThe extract is dried over sodium sulfate
  5. customevaporated
  6. filtrationthe solid filtered of and
  7. customdried (vacuum)
  8. customA powder with mp. 103-105° C. is obtained

Sources & evidence

ORD record
ord-1cd1d1cbee6746bc99383690b7f9f84c
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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