Phthalimide → 2-[3-(Pyridin-3-yl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 915656Notes

Reaction equation

HRID 915656 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][CH2:38][CH2:39]O)[CH:32]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(Cl)Cl.O>[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][CH2:38][CH2:39][N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH:32]=1

Participants

8

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 178613-PyridinepropanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 135575522-[3-(Pyridin-3-yl)propyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Cool a mixture of phthalimide (5.4 g, 37 mmol) and PPh3 (9.6 g, 37 mmol) in tetrahydrofuran (80 mL) to 0° C. Add dropwise a solution of 3-pyridine propanol (5.0 g, 37 mmol) and diethyl azodicarboxylate (5.8 mL, 37 mmol) in tetrahydrofuran (50 mL). After 2 hours, dilute the reaction mixture with methylene chloride (100 mL), and water (100 mL). Wash the organic layer with water (100 mL), then brine (100 mL). Dry over magnesium sulfate, filter and concentrate to afford 2-(3-pyridin-3-yl-propyl)isoindole-1,3-dione as a yellow solid which can be used without further purification.

Workup

  1. temperatureCool
  2. washWash the organic layer with water (100 mL)
  3. dry with materialDry over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-8feb6a2977a14896aa3aae19909ac31f
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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