3-[3-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)propyl]-1-(phenylmethyl)pyridinium bromide → 2-[3-[1-(phenylmethyl)-3-piperidinyl]propyl]-1H-isoindole-1,3(2H)-dione
Reaction equation
[Br-].[O:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]1[CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[N+:18]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:20][CH:21]=1>[Pt]=O.C(O)(=O)C>[C:23]1([CH2:22][N:18]2[CH2:19][CH2:20][CH2:21][CH:16]([CH2:15][CH2:14][CH2:13][N:4]3[C:5](=[O:12])[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:3]3=[O:2])[CH2:17]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 1.10 g (2.5 mmol) of 3-[3-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)propyl]-1-(phenylmethyl)pyridinium bromide, 50 mL of glacial acetic acid and 0.11 g of platinum oxide was hydrogenated at room temperature and atmospheric pressure for 6 hours with rapid stirring. The reaction mixture was filtered and concentrated, and the residue was dissolved in water. The aqueous solution was made strongly basic with aqueous potassium hydroxide and extracted several times with ethyl acetate. The combined organic extracts were washed with a saturated sodium bicarbonate solution and a saturated sodium chloride solution, dried and evaporated to give 0.77 g of 2-[3-[1-(phenylmethyl)-3-piperidinyl]propyl]-1H-isoindole-1,3(2H)-dione as a yellow oil.