N-3-Bromopropylphthalimide → N-[3-(3-piperidinomethylphenoxy)propyl]phthalimide

HRID 236261Notes

Reaction equation

HRID 236261 reaction equation
[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][CH2:6][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)C=O>[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=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 8269741-(3-Hydroxybenzyl)piperidine

Product 1

HCID 12898565N-[3-(3-piperidinomethylphenoxy)propyl]phthalimideYield 88.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 150 ml of N,N-dimethylformamide was suspended 4.8 g of sodium hydride (52% purity), and 20.0 g of 3-piperidinomethylphenol was added in small portions with stirring under ice-cooling. After the addition, the resulting mixture was subjected to reaction at room temperature for 1 hour. To the reaction mixture thus obtained was added 28.0 g of N-(3-bromopropyl)phthalimide, and the resulting mixture was subjected to reaction for 24 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and 300 ml of water and 300 ml of chloroform were added to the resulting residue to dissolve the same. The organic layer was separated and then dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure to obtain 35.0 g (yield 88.5%) of oily N-[3-(3-piperidinomethylphenoxy)propyl]phthalimide.

Workup

  1. additionwas added in small portions
  2. temperaturecooling
  3. additionAfter the addition
  4. customthe resulting mixture was subjected to reaction at room temperature for 1 hour
  5. customTo the reaction mixture thus obtained
  6. customthe resulting mixture was subjected to reaction for 24 hours
  7. customAfter completion of the reaction
  8. customthe solvent was removed by distillation under reduced pressure, and 300 ml of water and 300 ml of chloroform
  9. additionwere added to the resulting residue
  10. dissolutionto dissolve the same
  11. customThe organic layer was separated
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customafter which the solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-7b74214388e8488c8bf929a13e7fbba7
Source dataset
uspto-grants-1987_02
Patent number
US04643849

Reaction notes

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