Reaktion #2206208

Reaktionsgleichung

N-(o-ethoxycarbonylphenyl)-trans-4-guanidinomethylcyclohexanecarboxamide hydrochloride

methanol

NaOH

→

N-(o-carboxyphenyl)-trans-4-guanidinomethylcyclohexanecarboxamide hydrochloride

Ausbeute 86.3%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   Sonstigethe white precipitates
3. 3
   Sonstigeare separated by filtration
4. 4
   workup.DISSOLUTIONdissolved
5. 5
   workup.ADDITIONby adding
6. 6
   SonstigeAfter evaporation of the solvent under reduced pressure
7. 7
   Sonstigethe residue is recrystallized from water-methanol (4:1)
8. 8
   Sonstigethe crystals thus obtained
9. 9
   Sonstigeare again recrystallized from water-methanol (3:1)

Vorschrift

To N-(o-ethoxycarbonylphenyl)-trans-4-guanidinomethylcyclohexanecarboxamide hydrochloride (25.4 g, 0.063 mole) (which is prepared in the same manner as described in Example 1) is added methanol (130 ml), and the mixture is heated to 50° C., and thereto is added a solution of NaOH (7.16 g, 0.179 mole) in water (65 ml), and the mixture is stirred at 50°-60° C. for 45 minutes. The reaction mixture is ice-cooled, and the white precipitates are separated by filtration, suspended in methanol (100 ml) and dissolved by adding thereto 4N-hydrochloric acid (21 ml). After evaporation of the solvent under reduced pressure, the residue is recrystallized from water-methanol (4:1), and the crystals thus obtained are again recrystallized from water-methanol (3:1) to give N-(o-carboxyphenyl)-trans-4-guanidinomethylcyclohexanecarboxamide hydrochloride (19.3 g) as white crystals. The physical data of this compound are identical with those of N-(o-carboxyphenyl)-trans-4-guanidinomethylcyclohexanecarboxamide hydrochloride as obtained in Example 3.

Quelle