反应 #2271699

反应方程式

sodium hydride

1-bromo-3-chloropropane

1-(4-hydroxy-3-methylamino-phenyl)ethanone

→

beige solid

1-[4-(3-chloropropoxy)-3-methylaminophenyl]ethanone

溶剂

dimethylformamide

dimethylformamide

dimethylformamide

反应条件

后处理

1. 1
   温度cooled to 0° in an ice-salt bath
2. 2
   workup.ADDITIONwas added
3. 3
   其他did not rise above 3° C
4. 4
   workup.ADDITIONAfter the addition
5. 5
   温度The reaction was cooled to 5° C.
6. 6
   workup.ADDITIONAfter this addition
7. 7
   其他the ice bath was removed
8. 8
   workup.STIRRINGthe reaction was stirred at ambient temperature for 2.5 hours
9. 9
   workup.ADDITIONWater (75 ml) was carefully added
10. 10
    workup.STIRRINGafter stirring vigorously for 5 minutes
11. 11
    workup.WAITthe reaction was left
12. 12
    workup.WAITto stand overnight
13. 13
    萃取The aqueous mixture was extracted with ethyl acetate
14. 14
    萃取the ethyl acetate extract
15. 15
    洗涤was washed with water
16. 16
    干燥dried with MgSO4
17. 17
    浓缩concentrated
18. 18
    其他to yield 3.9 of a dark solid
19. 19
    其他The compound was purified by preparative HPLC

实验过程

To a stirred suspension of sodium hydride (0.87 g, 18.2 mmol of a 50% oil dispersion) in dimethylformamide (25 ml) under nitrogen and cooled to 0° in an ice-salt bath was added, dropwise, a solution or 1-(4-hydroxy-3-methylamino-phenyl)ethanone (3.0 g, 18.2 mmol) dissolved in dimethylformamide (55 ml) so that the temperature did not rise above 3° C. After the addition was complete, the reaction was stirred for 80 minutes of ambient temperature. The reaction was cooled to 5° C. and a solution of 1-bromo-3-chloropropane (3.1 g, 0.0120 mmol) in dimethylformamide (20 ml) was added dropwise. After this addition was complete, the ice bath was removed and the reaction was stirred at ambient temperature for 2.5 hours. Water (75 ml) was carefully added and after stirring vigorously for 5 minutes, the reaction was left to stand overnight. The aqueous mixture was extracted with ethyl acetate and the ethyl acetate extract was washed with water, dried with MgSO4, and concentrated to yield 3.9 of a dark solid. The compound was purified by preparative HPLC to afford 2.4 g of a beige solid. This was combined with an additional sample (3.8 g was total) and two consecutive recrystallizations from ethanol gave 2.1 g (31%) or 1-[4-(3-chloropropoxy)-3-methyl-aminophenyl]ethanone as a fluffy, beige solid, m.p.=115°-117° C. ANALYSIS: Calculated for C12H16ClNO2: 59. 63%C 6.67%H 5.69%N Found 59.49%C 6.64%H 5.79%N

来源