N-3-Bromopropylphthalimide → 2-[3-[3-(4morpholinylmethyl)phenoxy]propyl]-1H-isoindole-1,3(2H)-dione

HRID 1154721노트

반응식

HRID 1154721 반응식
[H-].[Na+].[N:3]1([CH2:9][C:10]2[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.Br[CH2:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31]>CN(C=O)C>[N:3]1([CH2:9][C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[O:16][CH2:18][CH2:19][CH2:20][N:21]2[C:25](=[O:26])[C:24]3[C:23](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:22]2=[O:31])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

참가 물질

5

반응물 3

HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 132775773-(Morpholinomethyl)phenol

생성물 1

HCID 133908182-[3-[3-(4morpholinylmethyl)phenoxy]propyl]-1H-isoindole-1,3(2H)-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To 1.58 g (0.033 moles) of 50% sodium hydride is added 15 ml DMF; then 6.3 g (0.033 moles) of 3-(4-morpholinylmethyl)phenol, dissolved in 30 ml DMB, is added dropwise to the stirred suspension at room temperature. This mixture is stirred 20 minutes and then N-(3-bromopropyl)-phthalimide, 9 g. (0.033 moles) is added to the mixture and stirred. A clear, amber solution results. After 2 hours, this solution is poured into ice-water and extracted with 100 ml of chloroform. The organic layer is washed once with 100 ml 5%NaOH, and once with 100 ml water, dried over MgSO4, filtered and evaporated. The residue is dissolved in ether and washed again with 50 ml water. Then the organic layer is dried over MgSO4, filtered and evaporated. The residue rapidly forms a white solid. This is recrystallized from acetonitrile, m.p. 90°-93° C. (yield=39 g).

후처리

  1. additionis added dropwise to the stirred suspension at room temperature
  2. addition(0.033 moles) is added to the mixture
  3. stirringstirred
  4. customA clear, amber solution results
  5. waitAfter 2 hours
  6. extractionextracted with 100 ml of chloroform
  7. washThe organic layer is washed once with 100 ml 5%NaOH
  8. dry with materialonce with 100 ml water, dried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. dissolutionThe residue is dissolved in ether
  12. washwashed again with 50 ml water
  13. dry with materialThen the organic layer is dried over MgSO4
  14. filtrationfiltered
  15. customevaporated
  16. customThis is recrystallized from acetonitrile, m.p. 90°-93° C. (yield=39 g)

출처 및 근거

ORD 기록
ord-ce22eb94111e455484dcf937bb4eb2db
출처 데이터셋
uspto-grants-1984_12
특허 번호
US04490527

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