Phthalimide → N-[3-(4-Pyridyl)propyl]phthalimide

HRID 915657Notes

Reaction equation

HRID 915657 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][C:34]([CH2:37][CH2:38][CH2:39]O)=[CH:33][CH:32]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[N:31]1[CH:36]=[CH:35][C:34]([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:33][CH:32]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 729234-PyridinepropanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 12015796N-[3-(4-Pyridyl)propyl]phthalimide

Reagents, catalysts & solvents 1

HCID 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 4-pyridine propanol (5.0 g, 37 mmol) and diethyl azodicarboxylate (5.8 mL, 37 mmol) in tetrahydrofuran (55 mL). After 2 hours warming to room temperature, concentrate the reaction mixture to a brown paste and perform flash-chromatography on silica gel eluting with 20% of a 80:18:2 CHCl3/MeOH/concentrated NH4OH) solution in methylene chloride to afford 2-(3-pyridin-4-yl-propyl)isoindole-1,3-dione as a yellow solid. TLC (SiO2): Rf=0.68 [20% of a 80:18:2 CHCl3/MeOH/concentrated NH4OH solution in methylene chloride].

Workup

  1. temperatureCool
  2. concentrationconcentrate the reaction mixture to a brown paste

Sources & evidence

ORD record
ord-e692b765a1854c8eb413c3c0ab2884b7
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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