Water → 2-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylbenzamide

HRID 2294142Notes

Reaction equation

HRID 2294142 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[CH2:11][CH2:10]1)(=O)=O.[NH2:23][C:24]1[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=1[C:26]([N:28]([CH3:30])[CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:12]1[CH2:13][CH2:14][N:9]([CH2:8][CH2:7][CH2:6][NH:23][C:24]2[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=2[C:26]([N:28]([CH3:30])[CH3:29])=[O:27])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 47781752-Amino-N,N-dimethylbenzamideHCID 108061843-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl methanesulfonate

Product 1

HCID 105728542-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylbenzamideYield 62.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl methanesulfonate (2 g, 6.06 mmol), 2-amino-N,N-dimethylbenzamide (1 g, 6.06 mmol), prepared as in Example 22, and potassium carbonate (2.1 g, 15 mmol) in 50 mL of acetonitrile was heated at reflux for 30 hours. The mixture was poured into water and extracted with ethyl acetate. The organic phase was dried (K2CO3) and concentrated. The residue was purified on silica gel by flash chromatography eluting with 6% methanol/methylene chloride to give 2-{3-[4-(2-methoxyphenyl)-piperazin-1-yl]propylamino}-N,N-dimethylbenzamide (1.5 g, 3.78 mmol).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (K2CO3)
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel by flash chromatography
  7. washeluting with 6% methanol/methylene chloride

Sources & evidence

ORD record
ord-a35e787fc9cd4026ba396122fd1e6cab
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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