1-(4-Pyridyl)piperazine → HCID 9228479, compound

HRID 427440Notes

Reaction equation

HRID 427440 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[C:13]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)#[N:14]>ClCCl.C(N(CC)CC)C>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([C:19](=[O:20])[C:18]3[CH:22]=[CH:23][C:15]([C:13]#[N:14])=[CH:16][CH:17]=3)[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 705171-(4-Pyridyl)piperazineHCID 801724-Cyanobenzoyl chloride

Product 1

HCID 9228479HCID 9228479, compoundYield 28.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 1-(4-pyridyl)piperazine (0.49 g) in dry dichloromethane (20 ml) and triethylamine (0.7 ml) was treated slowly with a solution of 4-cyanobenzoyl chloride (0.50 g) in dry dichloromethane (30ml). The reaction mixture was then stirred under argon for 2 hours. The dichloromethane solvent was removed by evaporation and the residue dissolved in ethyl acetate. The organic extracts were then washed with aqueous sodium hydrogen carbonate solution, water, brine, dried (Na2SO4) and evaporated to give a colourless oil which was crystallised from ethyl acetate/isohexane to afford 1-(4-pyridyl)4-(4-cyanobenzoyl)piperazine (0.25 g) as a solid, m.p. 164-165° C.; microanalysis, found: C, 69.7; H, 5.6; N, 18.5%; C17H16N4O requires: C, 69.8; H, 5.52; N, 19.2%; NMR: (CDCl3) 3.38(bs,4H), 3.75(bs,4H), 6.67(dd,2H), 7.56(dd,2H), 7.76(dd,2H), 8.32(dd,2H): MS: m/z 293 (MH)+.

Workup

  1. customThe dichloromethane solvent was removed by evaporation
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic extracts were then washed with aqueous sodium hydrogen carbonate solution, water, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give a colourless oil which
  7. customwas crystallised from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-df74573bf3ff4ebabe2d15c60d5fa9ed
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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