反应详情

A solution 11.8 g (0.04 mole) of 3-(2,3-dichlorophenoxy)-1-pyrrolidinecarbonyl chloride in 50 ml of chloroform was stirred at 5° C. in an ice bath while the following were added in order: 25 g of ice, 5.52 g of potassium carbonate and 3.87 g (0.044 mole) of N,N-dimethylethylenediamine. The resulting mixture was stirred for 20 hours and worked up by adding additional water followed by separation of the organic phase. The chloroform solution was dried over magnesium sulfate, filtered and concentrated in vacuo to a dark amber oil, 14 g, which solidified on standing. TLC analysis (10% methanol/chloroform) showed 3 spots; therefore, the crude product was chromatographed on 50 g of Fluorisil. Elution with chloroform gave a dark forerun which was discarded, the main portion was collected and rechromatographed through a 50 g Florisil column. The column was washed with 200 ml of methanol and the 2 fractions (chloroform and methanol) were combined before concentrating on a rotary evaporator to give a light amber oil which solidified. Recrystallization from isopropyl ether gave a beige crystalline product; 4.5 g (34%), m.p. 94°-95° C.

1. additionwere added in order
2. customfollowed by separation of the organic phase
3. dry with materialThe chloroform solution was dried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo to a dark amber oil, 14 g, which
6. customtherefore, the crude product was chromatographed on 50 g of Fluorisil
7. washElution with chloroform
8. customgave a dark forerun which
9. customthe main portion was collected
10. customrechromatographed through a 50 g Florisil column
11. washThe column was washed with 200 ml of methanol
12. concentrationbefore concentrating on a rotary evaporator
13. customto give a light amber oil which
14. customRecrystallization from isopropyl ether
15. customgave a beige crystalline product