Reaktion #1261070

Reaktionsgleichung

acetic acid

1-methyl-2-imidazole carboxaldehyde

sodium cyanoborohydride

amino methylbenzoic acid methyl ester

→

compound

4-{[bis(1-methyl-1H-imidazol-2-ylmethyl)amino]methyl}-benzoic acid

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter completion of the reaction
2. 2
   workup.DISTILLATIONthe solvent was distilled off
3. 3
   workup.DISSOLUTIONthe residue was then dissolved in chloroform
4. 4
   Waschenby washing with a 1 mol/l sodium hydroxide solution
5. 5
   TrocknenThe solution was dried with anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off
7. 7
   workup.DISSOLUTIONSubsequently, the residue was dissolved in methanol (6.0 ml)
8. 8
   workup.ADDITIONadded with 1 mol/l sodium hydroxide
9. 9
   workup.STIRRINGby stirring at room temperature for 6 hours
10. 10
    SonstigeAfter completion of the reaction, 1 mol/l hydrochloric acid (6.0 ml)
11. 11
    workup.ADDITIONwas added
12. 12
    workup.DISTILLATIONthe solvent was distilled off
13. 13
    workup.ADDITIONAfter that, ethanol was added
14. 14
    Sonstigeto remove insoluble matter
15. 15
    workup.DISTILLATIONthe solvent was distilled off
16. 16
    Sonstigethe residue was then dried

Vorschrift

Commercially available amino methylbenzoic acid methyl ester (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (278 mg) was dissolved in methanol (9 ml). Then, the solution was added with 1-methyl-2-imidazole carboxaldehyde (manufactured by Aldrich Corporation) (407 mg) and sodium cyanoborohydride (317 mg), and then adjusted to about pH 5 with acetic acid, followed by stirring at room temperature for 3 days. After completion of the reaction, the solvent was distilled off and the residue was then dissolved in chloroform, followed by washing with a 1 mol/l sodium hydroxide solution. The solution was dried with anhydrous sodium sulfate, and the solvent was distilled off. Subsequently, the residue was dissolved in methanol (6.0 ml) and then added with 1 mol/l sodium hydroxide, followed by stirring at room temperature for 6 hours. After completion of the reaction, 1 mol/l hydrochloric acid (6.0 ml) was added and the solvent was distilled off. After that, ethanol was added to remove insoluble matter, the solvent was distilled off, and the residue was then dried, thereby obtaining the subject compound (519 mg) as a pale-yellow foamy substance.

Quelle