Trifluoroacetic acid → 5'-Chloro-3,5-dimethyl-2'-(piperazin-1-yl)-2,4'-bipyridine

HRID 2172859Notes

Reaction equation

HRID 2172859 reaction equation
[Cl:1][C:2]1[C:3]([C:21]2[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][N:22]=2)=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl.CO>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:21]2[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][N:22]=2)=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 67508218Tert-butyl 4-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperazine-1-carboxylate

Product 1

HCID 675095955'-Chloro-3,5-dimethyl-2'-(piperazin-1-yl)-2,4'-bipyridineYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(5′-chloro-3,5-dimethyl-2,4′-bipyridin-2′-yl)piperazine-1-carboxylate (5.6 g, 14 mmol) in CH2Cl2 (50 mL) was added TFA (25 mL). Then the mixture was stirred for 18 hours. TLC (CH2Cl2/MeOH=10:1) showed the starting material was consumed completely. After removal of the solvent, the residue was dissolved in CH2Cl2 (180 mL), basified with 3 N aq. NaOH until pH=11, washed with brine (40 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford title compound (4.1 g, 97%) as orange oil.

Workup

  1. customwas consumed completely
  2. customAfter removal of the solvent
  3. dissolutionthe residue was dissolved in CH2Cl2 (180 mL)
  4. washwashed with brine (40 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c2c7165758e4cbda236d485b93c263e
Source dataset
uspto-grants-2015_06
Patent number
US09056865B2

Reaction notes

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