반응 #319505

반응 방정식

4-(1H-imidazol-1-yl)phenol

potassium hydroxide

2-diethylaminoethyl chloride hydrochloride

→

title compound

N,N-Diethyl-2-[4-(1H-imidazol-1-yl)phenoxy]ethanamine

용매

methanol

반응 조건

후처리

1. 1
   온도to reflux under nitrogen overnight
2. 2
   온도Cool the mixture
3. 3
   농축concentrate in vacuo
4. 4
   workup.DISSOLUTIONDissolve the residue in water (50mL)
5. 5
   세척Wash with 2×100 mL of methylene chloride
6. 6
   건조dry (Na2SO4)
7. 7
   농축concentrate in vacuo
8. 8
   workup.DISSOLUTIONThis residue is dissolved in ethanol
9. 9
   workup.ADDITION37% hydrochloric acid is added until pH=1.0
10. 10
    농축Concentration
11. 11
    기타affords crystals which
12. 12
    기타are recrystallized from isopropanol/ethanol (ca. 4+1)
13. 13
    기타Drying at 80° C. for 5 hr at 1.0 mm

실험 절차

Dissolve 4-(1H-imidazol-1-yl)phenol (4.02 g, 25.1 mmol) in methanol (100 mL) containing potassium hydroxide (3.52 g, 62.74 mmol). Add 2-diethylaminoethyl chloride hydrochloride to this mixture and heat to reflux under nitrogen overnight. Cool the mixture and concentrate in vacuo. Dissolve the residue in water (50mL) and adjust the pH to 13 with 1N NaOH solution. Wash with 2×100 mL of methylene chloride, combine, dry (Na2SO4) and concentrate in vacuo. This residue is dissolved in ethanol and 37% hydrochloric acid is added until pH=1.0. Concentration affords crystals which are recrystallized from isopropanol/ethanol (ca. 4+1). Drying at 80° C. for 5 hr at 1.0 mm give the title compound.

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