반응 #217870

반응 방정식

dimethylacetamide

6-chloronicotinamide

4-(2-benzylamino-ethyl)-phenol

potassium carbonate

→

6-[4-(2-benzylamino-ethyl)-phenoxy]-nicotinamide

수율 127.9%

용매

isooctane

반응 조건

후처리

1. 1
   온도heat
2. 2
   기타the reaction
3. 3
   온도to reflux under nitrogen for 6 h
4. 4
   온도Cool the reaction
5. 5
   기타mixtures to room temperature
6. 6
   여과filter off the solids
7. 7
   농축concentrate most of the solvent off on a rotary evaporator
8. 8
   workup.ADDITIONadd 1N hydrochloric acid (200 mL)
9. 9
   여과filter off the precipitate
10. 10
    세척washing with ethyl acetate
11. 11
    workup.DISSOLUTIONDissolve the solid in 400 mL
12. 12
    workup.ADDITIONTo this solution add 5N sodium hydroxide (35 mL)
13. 13
    여과Filter
14. 14
    세척wash with water

실험 절차

Add 6-chloronicotinamide (7.03 g, 44.90 mmol) to a stirred solution of 4-(2-benzylamino-ethyl)-phenol (10.10 g, 44.43 mmol), potassium carbonate (15.35 g, 111.1 mmol), dimethylacetamide (138 mL), and isooctane (16 mL). Using a Dean-Stark trap, heat the reaction to reflux under nitrogen for 6 h. Cool the reaction mixtures to room temperature, filter off the solids, and concentrate most of the solvent off on a rotary evaporator. Take the residue up in ethyl acetate (200 mL) and add 1N hydrochloric acid (200 mL). Stir for 15 minutes and filter off the precipitate washing with ethyl acetate. Dissolve the solid in 400 mL of boiling 1:1 methanol/water. To this solution add 5N sodium hydroxide (35 mL) and allow the solution to cool to room temperature. Filter and wash with water to yield 19.74 g (83%) of 6-[4-(2-benzylamino-ethyl)-phenoxy]-nicotinamide: mass spectrum (ion spray): m/z=348.1 (M+1); 1H NMR (CDCl3): 8.58 (d, 1H), 8.15 (dd, 1H), 7.34-7.24 (m, 7H), 7.06 (d, 2H), 6.93 (d, 1H), 6.08 (br s, 2H), 3.82 (s, 2H), 2.92 (t, 2H), 2.84 (t, 2H), 1.33 (br s, 1H).

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