Benzyl Bromide → HCID 42645471, compound

HRID 38254Notes

Reaction equation

HRID 38254 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[CH:11]=[C:12]([NH:22][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:2]([N:19]1[CH2:20][CH2:21][N:16]([C:15]2[CH:14]=[CH:13][C:12]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:11][C:10]=2[Cl:9])[CH2:17][CH2:18]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67441344N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide

Product 1

HCID 42645471HCID 42645471, compoundYield 192.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to Scheme 5 Step 5 Method B: A suspension of (bromomethyl)benzene (0.61 mmol, 74 μL), N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide (0.51 mmol, 161 mg) and of K2CO3 (0.51 mmol, 70 mg) in ACN (3 mL) was stirred at 80° C. for 30 minutes. After evaporation of the solvent, water and AcOEt were added. The aqueous phase was extracted with AcOEt. The organic phase was washed with brine, was dried over Na2SO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using DCM/AcOEt (80:20) as eluent and finally crystallized in pentane to obtain N-(4-(4-benzylpiperazin-1-yl)-3-chlorophenyl)picolinamide (0.98 mmol, 40 mg, 20%) as a white solid.

Workup

  1. customAfter evaporation of the solvent, water and AcOEt
  2. additionwere added
  3. extractionThe aqueous phase was extracted with AcOEt
  4. washThe organic phase was washed with brine
  5. dry with materialwas dried over Na2SO4
  6. filtrationwas filtered
  7. concentrationwas concentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography over silica gel
  9. customfinally crystallized in pentane

Sources & evidence

ORD record
ord-ffabc75a608944ac845f7dfd6409fe52
Source dataset
uspto-grants-2013_09
Patent number
US08524726B2

Reaction notes

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