Hydrochloric Acid → 2-(Piperidin-3-yl)-1H-isoindole-1,3(2H)-dione

HRID 1415566Notes

Reaction equation

HRID 1415566 reaction equation
NC1CCCNC1.C1(=O)OC(=O)C2=CC=CC=C12.C(C1C=CC=CC=1C([N:26]1[CH2:31][CH2:30][CH2:29][CH:28]([N:32]2[C:36](=[O:37])[C:35]3=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]3[C:33]2=[O:42])[CH2:27]1)=O)(O)=O.Cl>>[C:33]1(=[O:42])[N:32]([CH:28]2[CH2:29][CH2:30][CH2:31][NH:26][CH2:27]2)[C:36](=[O:37])[C:35]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]12

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6811Phthalic AnhydrideHCID 148119Piperidin-3-amineHCID 214828121-(2-Carboxybenzoyl)-3-phthalimidopiperidine

Product 1

HCID 199722632-(Piperidin-3-yl)-1H-isoindole-1,3(2H)-dione

Procedure

A mixture of 10 g. of 3-aminopiperidine and 29.6 g. of phthalic anhydride is heated at 150° C. for 30 minutes. This mixture which contains 1-(2-carboxybenzoyl)-3-phthalimidopiperidine is heated at reflux with 500 ml. of 6N hydrochloric acid for two hours. The aqueous phase is extracted with ether and then concentrated in vacuo. The residue is extracted with dilute aqueous sodium hydroxide solution and methylene chloride. The organic phase is dried and concentrated in vacuo to give 3-phthalimidopiperidine.

Workup

  1. additionA mixture of 10 g
  2. temperatureis heated
  3. temperatureat reflux with 500 ml
  4. extractionThe aqueous phase is extracted with ether
  5. concentrationconcentrated in vacuo
  6. extractionThe residue is extracted with dilute aqueous sodium hydroxide solution and methylene chloride
  7. customThe organic phase is dried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8757a0ce6bb4892ae6327e0a4d9eeb0
Source dataset
uspto-grants-1977_01
Patent number
US04005208

Reaction notes

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