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Triethylamine → Tert-butyl 4-(2-chloro-4-(picolinamido)phenyl)piperazine-1-carboxylate

HRID 38251
Notes
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Reaction equation

HRID 38251 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].CCN(CC)CC.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)=[C:21]([Cl:38])[CH:20]=1>C(Cl)Cl>[Cl:38][C:21]1[CH:20]=[C:19]([NH:18][C:8](=[O:9])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[CH:24]=[CH:23][C:22]=1[N:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 18783766Tert-Butyl 4-(4-Amino-2-Chlorophenyl)Piperazine-1-Carboxylate

Product 1

HCID 67441071Tert-butyl 4-(2-chloro-4-(picolinamido)phenyl)piperazine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

According to Scheme 5 Step 3: Picolinoyl chloride hydrochloride (3.68 mmol, 656 mg) and Et3N (7.37 mmol, 1.03 mL) were added to a solution of tert-butyl 4-(4-amino-2-chlorophenyl)piperazine-1-carboxylate (2.46 mmol, 766 mg) in DCM (40 mL) at 0° C. The reaction mixture was stirred at room temperature for 1 hour. The organic phase was washed with a saturated solution of NaHCO3. 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 to afford tert-butyl 4-(2-chloro-4-(picolinamido)phenyl)piperazine-1-carboxylate (2.46 mmol, 1.02 g, 100%).

Workup

  1. washThe organic phase was washed with a saturated solution of NaHCO3
  2. extractionThe aqueous phase was extracted with AcOEt
  3. washThe organic phase was washed with brine
  4. dry with materialwas dried over Na2SO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-fbce41f4d7ee430591e03e6b74442165
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524726B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes