N-3-Bromopropylphthalimide → HCID 20138928, compound

HRID 280149Notes

Reaction equation

HRID 280149 reaction equation
CC(C)([O-])C.[K+].[OH:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][CH:13]2[N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.Br[CH2:25][CH2:26][CH2:27][N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38]>CN(C)C=O>[C:29]1(=[O:38])[N:28]([CH2:27][CH2:26][CH2:25][O:7][C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH2:10][CH2:11][CH2:12][CH:13]3[N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]12

Participants

5

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 13519501HCID 13519501, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20138928HCID 20138928, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium t-butoxide (7.8 g) is added to a stirred solution of 5-hydroxy-1-morpholinyl-1,2,3,4-tetrahydronaphthalene (14.7 g) dissolved in dimethylformamide (150 ml) and the reaction solution stirred for a few minutes. N-(3-bromopropyl) phthalimide (33.8 g) is added to the reaction mixture and stirring is continued at RT for 2 days. The reaction mixture is partitioned between H2O and ether, the layers separated and the aqueous layer adjusted to a pH>10 with sodium hydroxide solution and extracted with additional diethyl ether. The combined ether layers are washed with H2O and aqueous 5% hydrochloric acid. The acidic aqueous extracts are made strongly alkaline with sodium hydroxide solution, resulting in an oily precipitate which is extracted with ether and methylene chloride. The combined organic layers are washed with 5% aqueous sodium hydroxide and saturated sodium chloride, dried over sodium sulfate, filtered, and evaporated, resulting in 22.6 g of an amber oil as the crude product used in the next step.

Workup

  1. stirringstirring
  2. customThe reaction mixture is partitioned between H2O and ether
  3. customthe layers separated
  4. extractionextracted with additional diethyl ether
  5. washThe combined ether layers are washed with H2O and aqueous 5% hydrochloric acid
  6. customresulting in an oily precipitate which
  7. extractionis extracted with ether and methylene chloride
  8. washThe combined organic layers are washed with 5% aqueous sodium hydroxide and saturated sodium chloride
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-3bbd5d1275c445c296f239a643645044
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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