반응 #4894

반응 방정식

hydrochloric acid

sodium hydroxide

2-[(1-methyl-3-pyrrolidinyl)oxy]benzamide

→

2-(2-Chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)-one

용매

water

반응 조건

후처리

1. 1
   온도to reflux for 18 hr
2. 2
   여과the solution filtered
3. 3
   농축concentrated
4. 4
   여과filtered
5. 5
   농축The filtrate was concentrated
6. 6
   기타the residue (which crystallized)
7. 7
   온도was refluxed with 300 ml of thionyl chloride for 0.5 hr
8. 8
   농축and concentrated in vacuo
9. 9
   workup.DISSOLUTIONThe residue was dissolved in 300 ml of chloroform
10. 10
    workup.DISSOLUTIONThe residue was redissolved in chloroform
11. 11
    workup.ADDITION150 ml of triethyl amine added
12. 12
    온도the mixture refluxed 1 hr
13. 13
    농축The solution was concentrated in vacuo
14. 14
    기타the residue partitioned between 400 ml of ethyl acetate, 400 ml of isopropyl ether and 500 ml of dilute hydrochloric acid
15. 15
    세척The organic layer was washed twice with water and once with dilute sodium hydroxide
16. 16
    건조dried with sodium sulfate
17. 17
    농축concentrated
18. 18
    기타The residue was crystallized from isopropanol-water

실험 절차

To 54 g (1.35 mole) of sodium hydroxide in 800 ml of water was added 148 g (0.67 mole) of 2-[(1-methyl-3-pyrrolidinyl)oxy]benzamide and the mixture brought to reflux for 18 hr. The pH was adjusted to 7 with hydrochloric acid and the solution filtered and concentrated. The residue was boiled with 400 ml of isopropanol and filtered. The filtrate was concentrated and the residue (which crystallized) was refluxed with 300 ml of thionyl chloride for 0.5 hr. and concentrated in vacuo. The residue was dissolved in 300 ml of chloroform and the solvent boiled off in vacuo. The residue was redissolved in chloroform, 150 ml of triethyl amine added and the mixture refluxed 1 hr. The solution was concentrated in vacuo and the residue partitioned between 400 ml of ethyl acetate, 400 ml of isopropyl ether and 500 ml of dilute hydrochloric acid. The organic layer was washed twice with water and once with dilute sodium hydroxide, dried with sodium sulfate and concentrated. The residue was crystallized from isopropanol-water. Yield of product was 75 g (47%), m.p. 97°-107° C.

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