반응 #1747830

반응 방정식

LiAlH4

3-(4-methoxyphenyl)-propionic acid n-propyl amid

→

N-(3-(4-methoxyphenyl)-propyl)-N-propylamine

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도After refluxing for 12 h the mixture
2. 2
   기타excess hydride was destroyed by careful addition of water (10 mL), 5% aqueous NaOH (40 mL) and water (20 mL)
3. 3
   온도allowing reflux conditions
4. 4
   여과The hot slurry was filtered
5. 5
   세척the white precipitate was washed thoroughly with ethanol
6. 6
   기타Volatiles were evaporated
7. 7
   workup.DISSOLUTIONthe resulting oil dissolved in ethyl acetate (50 mL) what
8. 8
   추출was extracted with 0.5 N aqueous HCl (4×50 mL)
9. 9
   workup.ADDITIONby addition of 30% aqueous NaOH
10. 10
    추출extracted with ethyl acetate (4×50 mL)
11. 11
    세척washed with brine
12. 12
    건조dried (MgSO4)
13. 13
    기타evaporated to dryness
14. 14
    기타to give an oil that
15. 15
    기타partially crystallized in diethyl ether as the hydrochloride salt
16. 16
    기타Recrystallization from acetone/diethyl ether
17. 17
    기타gave white flacky crystalline material
18. 18
    기타Total yield (as free base)

실험 절차

To a stirred mixture of LiAlH4 (8.0 g, 200 mmol) in tetrahydrofuran (100 mL) was added dropwise a solution of 3-(4-methoxyphenyl)-propionic acid n-propyl amid (10.7 g, 49 mmol) (from a) above) in tetrahydrofuran (100 mL). After refluxing for 12 h the mixture was cooled to 50° C. and excess hydride was destroyed by careful addition of water (10 mL), 5% aqueous NaOH (40 mL) and water (20 mL) allowing reflux conditions. The hot slurry was filtered and the white precipitate was washed thoroughly with ethanol. Volatiles were evaporated and the resulting oil dissolved in ethyl acetate (50 mL) what was extracted with 0.5 N aqueous HCl (4×50 mL). The acidic phase was made alkaline (pH=9) by addition of 30% aqueous NaOH and extracted with ethyl acetate (4×50 mL). The organic layers were combined, washed with brine, dried (MgSO4) and evaporated to dryness to give an oil that partially crystallized in diethyl ether as the hydrochloride salt. Recrystallization from acetone/diethyl ether gave white flacky crystalline material. Total yield (as free base): 9.9 g, 48 mmol, 98%, mp 176-177° C. IR (neat) cm−1 2960, 2772, 1611, 1514; 1H-NMR (CDCl3) δ 9.46 (br s, 1H), 7.16 (d, 2H), 6.90 (d, 2H), 3.72 (s, 3H), 2.82 (br s, 4H), 2.59 (t, 2H), 2.15 (p, 2H), 1.83 (h, 2H), 0.89 (t, 3H) ppm; 13C-NMR (CDCl3) δ 156.6, 130.3, 127.7, 112.4, 53.7, 47.9, 45.66, 30.3, 25.9, 17.8, 9.7 ppm; MS (EI) m/z 207 (M+).

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