Thionyl Chloride → HCID 23291098, compound

HRID 365303Notes

Reaction equation

HRID 365303 reaction equation
S(Cl)([Cl:3])=[O:2].[N:5]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:6]=1[CH2:7]C(O)=O.[CH2:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)(Cl)Cl.CC(C)=O>[ClH:3].[CH2:19]([N:26]1[CH2:31][CH2:30][N:29]([C:7]([C:6]2[CH:11]=[CH:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:5]=2)=[O:2])[CH2:28][CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 759941-BenzylpiperazineHCID 47117842-(Quinolin-2-YL)acetic acid

Product 1

HCID 23291098HCID 23291098, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

Thionyl chloride (6 ml) was added to a suspension of quinaldinic acid (3.463 g, 20 mmol) in chloroform (40 ml). After the resulting mixture was heated under reflux and stirring for 6 hours, the solvent was distilled off. The residue was dissolved in acetone (50 ml), followed by the addition of a solution of N-benzylpiperazine (10.576 g, 60 mmol) in acetone (50 ml). The thus-obtained mixture was stirred for 1 hour. A deposited precipitate was removed, and the solvent was distilled off. The residue was dissolved in ethyl ether. The resulting solution was washed with an aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was dissolved in methanol, followed by the addition of concentrated hydrochloric acid (5 ml) for acidification. The solvent was distilled off and the thus-obtained residue was crystallized from a mixed solvent of ethanol and methanol, whereby 7.166 g of the title compound were obtained as white powder (yield: 97.5%).

Workup

  1. temperatureAfter the resulting mixture was heated
  2. temperatureunder reflux
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in acetone (50 ml)
  5. stirringThe thus-obtained mixture was stirred for 1 hour
  6. customA deposited precipitate was removed
  7. distillationthe solvent was distilled off
  8. dissolutionThe residue was dissolved in ethyl ether
  9. washThe resulting solution was washed with an aqueous solution of sodium chloride
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationThe solvent was distilled off
  12. dissolutionthe residue was dissolved in methanol
  13. additionfollowed by the addition of concentrated hydrochloric acid (5 ml) for acidification
  14. distillationThe solvent was distilled off
  15. customthe thus-obtained residue was crystallized from a mixed solvent of ethanol and methanol

Sources & evidence

ORD record
ord-0debfc1f785f4189a107bae53f0f3f30
Source dataset
uspto-grants-2000_10
Patent number
US06127360

Reaction notes

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