Phthalimide → 2-[6-(Morpholin-4-yl)pyridin-3-yl]methylisoindol-1,3-dione

HRID 1362676

Reaction equation

HRID 1362676 reaction equation
[N:1]1([C:7]2[N:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[N:1]1([C:7]2[N:12]=[CH:11][C:10]([CH2:13][N:19]3[C:15](=[O:25])[C:16]4[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:18]3=[O:20])=[CH:9][CH:8]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 2776465[6-(Morpholin-4-yl)pyridin-3-yl]methanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 669610022-[6-(Morpholin-4-yl)pyridin-3-yl]methylisoindol-1,3-dioneYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF (200 mL) solution of (6-(morpholin-4-yl)pyridine-3-yl)methanol (CA 388088-73-1) (3.2 g), phthalimide (3.64 g) and triphenylphosphine (6.49 g), diisopropylazodicarboxylate (5.43 mL) was added at 0° C. for 5 minutes. The reaction solution was concentrated under reduced pressure after 12-hour stirring at room temperature. 3.8 g of the title compound was obtained by the residue was purified by silica gel chromatography (heptane-ethyl acetate system).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure after 12-hour

Sources & evidence

ORD record
ord-d4be582774c34f87a07e1490b5f1bb88
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Linked notes

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