반응 #58591

반응 방정식

2-chloroacrylonitrile

N-benzyl ethanolamine

potassium tert-butoxide

THF

→

4-Benzyl-morpholine-2-carboxylic acid hydrochloride

수율 61.0%

용매

toluene

toluene

반응 조건

후처리

1. 1
   온도cooled to −5° C.
2. 2
   온도maintaining the temperature at −5° C. to 0° C
3. 3
   workup.STIRRINGThe mixture is post-agitated at about −5° C. to 0° C. for 1 h
4. 4
   기타quenched
5. 5
   workup.ADDITIONby adding water (45.9 mL)
6. 6
   기타The aqueous layer is separated
7. 7
   세척the toluene layer is washed with water (45.9 mL)
8. 8
   온도to warm to room temperature
9. 9
   농축The organic layer is then concentrated under reduced pressure at 40° C
10. 10
    workup.ADDITIONThen, the mixture is diluted with toluene (100 mL)
11. 11
    추출extracted with 6N HClaq (162 mL)
12. 12
    온도This aqueous layer is heated up to the
13. 13
    온도reflux for 1 h 30
14. 14
    workup.STIRRINGto stir at room temperature overnight
15. 15
    기타After crystallization of 91
16. 16
    여과the solid is filtered
17. 17
    세척rinsed with 6N HClaq (40 mL)
18. 18
    기타dried
19. 19
    기타at 40° C.

실험 절차

A 500 mL reactor under N2 is successively loaded with toluene (36.72 mL) and 2-chloroacrylonitrile (10.7 g, 122.23 mmol) at room temperature. Then, N-benzyl ethanolamine (18.36 g, 121.14 mmol) is added over 5 min and the reaction mixture is post-agitated at room temperature for 16 h. Then, the mixture is diluted with toluene (110.16 mL), cooled to −5° C. and 2M potassium tert-butoxide solution in THF (121.14 mmol) is slowly added over 30 min, maintaining the temperature at −5° C. to 0° C. The mixture is post-agitated at about −5° C. to 0° C. for 1 h, then quenched by adding water (45.9 mL). The aqueous layer is separated and the toluene layer is washed with water (45.9 mL) and then the mixture is allowed to warm to room temperature. The organic layer is then concentrated under reduced pressure at 40° C. Then, the mixture is diluted with toluene (100 mL) and extracted with 6N HClaq (162 mL). This aqueous layer is heated up to the reflux for 1 h 30, then the mixture is allowed to stir at room temperature overnight. After crystallization of 91, the solid is filtered, rinsed with 6N HClaq (40 mL) and dried under reduce pressure at 40° C. (19 g, yield=61%).

출처