Glyoxal → HCID 15053320, compound

HRID 1088824Notes

Reaction equation

HRID 1088824 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH2:13][S:14][C:15]2[NH:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH:6]([NH:24][CH3:25])[CH2:5][CH2:4]1)[CH3:2].[CH:26]([CH:28]=O)=[O:27]>CO>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH2:13][S:14][C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[CH:6]([N:24]([CH3:25])[CH2:28][CH2:26][OH:27])[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 14685792HCID 14685792, compound

Product 1

HCID 15053320HCID 15053320, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-ethyl-4-methylamino-8-(2-benzimidazolyl)thiomethyl-1,2,3,4-tetrahydroquinoline (900 mg) in methanol (20 ml) was added glyoxal (10 ml) and the mixture was stirred for 3 hours at room temperature. The solvent was distilled off and the resulting residue was dissolved in methanol, and to this mixture was added gradually sodium borohydride (1 g). After stirring the mixture for 1 hour at room temperature, the reaction mixture was concentrated. The resulting residue was extracted with dichloromethane and dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent was purified by silica gel column chromatography [eluent:dichloromethane-methanol (99:1)] to give 1-ethyl-4-[N-methyl-N-(2-hydroxyethyl)amino]-8-(2-benzimidazolyl)thiomethyl-1,2,3,4-tetrahydroquinoline (510 mg).

Workup

  1. distillationThe solvent was distilled off
  2. dissolutionthe resulting residue was dissolved in methanol
  3. additionto this mixture was added gradually sodium borohydride (1 g)
  4. stirringAfter stirring the mixture for 1 hour at room temperature
  5. concentrationthe reaction mixture was concentrated
  6. extractionThe resulting residue was extracted with dichloromethane
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe residue obtained
  9. distillationby distilling off the solvent
  10. customwas purified by silica gel column chromatography [eluent:dichloromethane-methanol (99:1)]

Sources & evidence

ORD record
ord-78833fa7cc8c496ba159734ca7c3f35a
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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