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

HRID 1708041Notes

Reaction equation

HRID 1708041 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]=1

Participants

4

Reactant 1

HCID 189971253-[3-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)propyl]-1-(phenylmethyl)pyridinium bromide

Product 1

HCID 189971342-[3-[1-(phenylmethyl)-3-piperidinyl]propyl]-1H-isoindole-1,3(2H)-dioneYield 85%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

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.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. dissolutionthe residue was dissolved in water
  5. extractionextracted several times with ethyl acetate
  6. washThe combined organic extracts were washed with a saturated sodium bicarbonate solution
  7. dry with materiala saturated sodium chloride solution, dried
  8. customevaporated

Sources & evidence

ORD record
ord-a58f7076f0b14d1fa1ff5e96df3699c4
Source dataset
uspto-grants-1994_10
Patent number
US05356906

Reaction notes

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