Sodium Iodide → 2-{3-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]propyl-amino}-N,N-dimethylbenzamide

HRID 2294148Notes

Reaction equation

HRID 2294148 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.Cl[CH2:17][CH2:18][CH2:19][NH:20][C:21]1[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=1[C:23]([N:25]([CH3:27])[CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH2:17][CH2:18][CH2:19][NH:20][C:21]3[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=3[C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[CH2:12][CH2:13]2)[CH:7]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2735754HCID 2735754, compoundHCID 214734352-(3-chloropropyl)amino-N,N-dimethylbenzamide

Product 1

HCID 214734652-{3-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]propyl-amino}-N,N-dimethylbenzamideYield 40.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(5-chloro-2-methoxyphenyl)piperazine (365 mg, 1.6 mmol), prepared as in Example 2, 2-(3-chloropropyl)amino-N,N-dimethylbenzamide (385 mg of crude mixture), prepared as in Example 28, potassium carbonate (550 mg, 3.98 mmol) and sodium iodide (240 mg, 1.6 mmol) in 20 mL of acetonitrile was heated at reflux for 18 hours. The mixture was poured into water and extracted with ethyl acetate (2×50 mL). The combined extract was washed with brine, dried (MgSO4) and concentrated. The residue was purified on silica gel by flash chromatography eluting with 6% methanol/methylene chloride to give 2-{3-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl ]propylamino}-N,N-dimethylbenzamide (280 mg, 0.65 mmol).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. extractionThe combined extract
  5. washwas washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel by flash chromatography
  9. washeluting with 6% methanol/methylene chloride

Sources & evidence

ORD record
ord-46b0388b059643fb89553b61e5746c23
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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