Реакция #1747830

Уравнение реакции

LiAlH4

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

→

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

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ТемператураAfter refluxing for 12 h the mixture
2. 2
   Другоеexcess hydride was destroyed by careful addition of water (10 mL), 5% aqueous NaOH (40 mL) and water (20 mL)
3. 3
   Температураallowing reflux conditions
4. 4
   ФильтрацияThe hot slurry was filtered
5. 5
   Промывкаthe white precipitate was washed thoroughly with ethanol
6. 6
   ДругоеVolatiles were evaporated
7. 7
   workup.DISSOLUTIONthe resulting oil dissolved in ethyl acetate (50 mL) what
8. 8
   Экстракцияwas extracted with 0.5 N aqueous HCl (4×50 mL)
9. 9
   workup.ADDITIONby addition of 30% aqueous NaOH
10. 10
    Экстракцияextracted with ethyl acetate (4×50 mL)
11. 11
    Промывкаwashed with brine
12. 12
    Сушкаdried (MgSO4)
13. 13
    Другоеevaporated to dryness
14. 14
    Другоеto give an oil that
15. 15
    Другоеpartially crystallized in diethyl ether as the hydrochloride salt
16. 16
    ДругоеRecrystallization from acetone/diethyl ether
17. 17
    Другоеgave white flacky crystalline material
18. 18
    ДругоеTotal yield (as free base)

Методика

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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