反応 #1747830

反応方程式

LiAlH4

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

→

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

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度After refluxing for 12 h the mixture
2. 2
   その他excess hydride was destroyed by careful addition of water (10 mL), 5% aqueous NaOH (40 mL) and water (20 mL)
3. 3
   温度allowing reflux conditions
4. 4
   ろ過The hot slurry was filtered
5. 5
   洗浄the white precipitate was washed thoroughly with ethanol
6. 6
   その他Volatiles were evaporated
7. 7
   workup.DISSOLUTIONthe resulting oil dissolved in ethyl acetate (50 mL) what
8. 8
   抽出was extracted with 0.5 N aqueous HCl (4×50 mL)
9. 9
   workup.ADDITIONby addition of 30% aqueous NaOH
10. 10
    抽出extracted with ethyl acetate (4×50 mL)
11. 11
    洗浄washed with brine
12. 12
    乾燥dried (MgSO4)
13. 13
    その他evaporated to dryness
14. 14
    その他to give an oil that
15. 15
    その他partially crystallized in diethyl ether as the hydrochloride salt
16. 16
    その他Recrystallization from acetone/diethyl ether
17. 17
    その他gave white flacky crystalline material
18. 18
    その他Total yield (as free base)

実験手順

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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