Hydrochloric Acid → 2-(Piperidin-4-yl)isoindoline-1,3-dione hydrochloride

HRID 972809Notes

Reaction equation

HRID 972809 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:25]>CO.C(O)(=O)C.[Pd]>[ClH:25].[C:15]1(=[O:24])[N:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 28262461-Benzyl-4-phthalimidopiperidine

Product 1

HCID 218825602-(Piperidin-4-yl)isoindoline-1,3-dione hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

16.0 Grams of 1-benzyl-4-phthalimido-piperidine were dissolved in 200 milliliters of 50% methanol/acetic acid and 25 milliliters of ethereal hydrogen chloride, and were hydrogenated at 60° C. and 60 psi in the presence of 2.0 grams of 10% palladium-on-charcoal catalyst. After 4 hours the reaction mixture was filtered while still hot and addition of ether gave 8.7 grams of 4-phthalimido-piperidine mono-hydrochloride. Melting point: 300° C. with decomposition.

Workup

  1. customwere hydrogenated at 60° C.
  2. filtrationAfter 4 hours the reaction mixture was filtered while still hot and
  3. additionaddition of ether

Sources & evidence

ORD record
ord-115f4086bd614219bdf9c5e769095c51
Source dataset
uspto-grants-1977_10
Patent number
US04053615

Reaction notes

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