Trifluoroacetic acid → 5-Methyl-6-(piperazin-1-yl)nicotinonitrile

HRID 2411235Notes

Reaction equation

HRID 2411235 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([C:21]#[N:22])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:20][C:19]1[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[N:15][CH:16]=[C:17]([CH:18]=1)[C:21]#[N:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66838837Tert-butyl 4-(5-cyano-3-methylpyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 673812745-Methyl-6-(piperazin-1-yl)nicotinonitrileYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(5-Cyano-3-methylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (2.45 g) described in Preparation Example 102 was dissolved in dichloromethane (15 mL), trifluoroacetic acid (5 mL) was added, and the mixture was stirred at room temperature for 6 hr. The solvent was evaporated from the reaction mixture, aqueous potassium carbonate solution was added, and the mixture was extracted with chloroform. The solvent was evaporated from the organic layer, the obtained residue was purified by NH-coated silica gel silica gel column chromatography (hexane:ethyl acetate) to give the title compound (1.07 g).

Workup

  1. customThe solvent was evaporated from the reaction mixture, aqueous potassium carbonate solution
  2. additionwas added
  3. extractionthe mixture was extracted with chloroform
  4. customThe solvent was evaporated from the organic layer
  5. customthe obtained residue was purified by NH-coated silica gel silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-298508514bce4dc5a76a5cde757382a4
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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