N-3-Bromopropylphthalimide → 4-(3-Phthalimidopropyloxy)pyridine

HRID 274681Notes

Reaction equation

HRID 274681 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Br[CH2:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[C:13]1(=[O:22])[N:12]([CH2:11][CH2:10][CH2:9][O:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]12

Participants

5

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178418642HCID 178418642, compound

Product 1

HCID 190790904-(3-Phthalimidopropyloxy)pyridineYield 16.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.76 g (50 mmol) of 4-hydroxypyridine and 14.75 g (55 mmol) of N-(3-bromopropyl)phthalimide in 80 ml of DMF was added 8.23 ml (55 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene. The mixture was stirred at room temperature for 6 hours. After the solvent was distilled off, the mixture was poured into water and extracted with ethyl acetate. The mixture was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 2.32 g of the desired compound (yield: 16.4% colorless crystals).

Workup

  1. distillationAfter the solvent was distilled off
  2. additionthe mixture was poured into water
  3. extractionextracted with ethyl acetate
  4. washThe mixture was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-2dafe5227f2d4b8c84b36f76fba6ae55
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Reaction notes

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