Hydrochloric Acid → N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide

HRID 38252Notes

Reaction equation

HRID 38252 reaction equation
Cl.O1CCOCC1.[Cl:8][C:9]1[CH:14]=[C:13]([NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:12]=[CH:11][C:10]=1[N:24]1[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]1>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[C:13]([NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:12]=[CH:11][C:10]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67441071Tert-butyl 4-(2-chloro-4-(picolinamido)phenyl)piperazine-1-carboxylate

Product 1

HCID 67441344N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamideYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to Scheme 5 Step 4: HCl 4 M in dioxane (12.3 mmol, 3.07 mL) was added to a solution of tert-butyl 4-(2-chloro-4-(picolinamido)phenyl)piperazine-1-carboxylate (2.46 mmol, 1.02 g) in DCM (10 mL). The reaction mixture was stirred at room temperature overnight. After evaporation, DCM was added and then a NaOH 1 M solution. The aqueous phase was extracted with DCM. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using cyclohexane/AcOEt (60:40) as eluent to afford N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide (0.97 mmol, 308 mg, 40%) as an orange solid.

Workup

  1. customAfter evaporation, DCM
  2. additionwas added
  3. extractionThe aqueous phase was extracted with DCM
  4. washThe organic phase was washed with brine
  5. dry with materialwas dried over MgSO4
  6. filtrationwas filtered
  7. concentrationwas concentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-85b89279c2bd4d0dafccb9dbb4150929
Source dataset
uspto-grants-2013_09
Patent number
US08524726B2

Reaction notes

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