Sodium Iodide → methyl 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazole-3-carboxylate

HRID 1907383Notes

Reaction equation

HRID 1907383 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[N:10]([CH3:11])[N:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=1.Cl.[S:17]1[CH:21]=[CH:20][C:19]2[C:22]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:23][CH:24]=[CH:25][C:18]1=2.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.CN(C=O)C>[S:17]1[CH:21]=[CH:20][C:19]2[C:22]([N:26]3[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][O:5][C:6]4[N:10]([CH3:11])[N:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=4)[CH2:28][CH2:27]3)=[CH:23][CH:24]=[CH:25][C:18]1=2

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 574825411-(1-Benzothiophen-4-yl)piperazine hydrochlorideHCID 57482559methyl 5-(3-chloropropoxy)-1-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 16044810methyl 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazole-3-carboxylateYield 71.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 5-(3-chloropropoxy)-1-methyl-1H-pyrazole-3-carboxylate (1.17 g, 5.0 mmol), 1-benzo[b]thiophen-4-yl piperazine hydrochloride (1.35 g, 5.3 mmol), potassium carbonate (1.74, 12.6 mmol) and sodium iodide (0.75 g, 5.0 mmol) were added to DMF (12 ml), and the mixture was stirred at 80° C. for 3 hours. The reaction solution was cooled to room temperature and water was added thereto, and then, extracted with ethyl acetate. The organic phase was washed with water and dried over magnesium sulfate. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:3→dichloromethane:methanol=100:3). The purified product was concentrated under reduced pressure to obtain a light yellow oily substance (1.97 g). The oily substance was allowed to stand still at room temperature to obtain a solid substance, which was washed with diisopropyl ether and dried to obtain methyl 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazole-3-carboxylate (1.49 g).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe reaction solution was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:3→dichloromethane:methanol=100:3)
  7. concentrationThe purified product was concentrated under reduced pressure
  8. customto obtain a light yellow oily substance (1.97 g)
  9. customto stand still at room temperature
  10. customto obtain a solid substance, which
  11. washwas washed with diisopropyl ether
  12. customdried

Sources & evidence

ORD record
ord-cd121e7e102e45cfb8f4625cd337f920
Source dataset
uspto-grants-2013_12
Patent number
US08598162B2

Reaction notes

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