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

HRID 1154721ノート

反応式

HRID 1154721 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ce22eb94111e455484dcf937bb4eb2db
出典データセット
uspto-grants-1984_12
特許番号
US04490527

反応ノート

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