N-3-Bromopropylphthalimide → HCID 20138928, compound

HRID 1905725Notes

Reaction equation

HRID 1905725 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-bd67ddec6f584c848a207b2ab92c5fb6
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

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