Hydrochloric Acid → 2-(Piperidin-4-yloxy)-isoindole-1,3-dione

HRID 2066895Notes

Reaction equation

HRID 2066895 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C)C.Cl>CCOCC>[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][N:15]2[C:16](=[O:25])[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]2=[O:24])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 3776IsopropanolHCID 21751544Tert-butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylate

Product 1

HCID 217515382-(Piperidin-4-yloxy)-isoindole-1,3-dioneYield 56.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.5 g of 69a was taken up with isopropanol (10 mL) and 1 mL of concentrated HCl. The mixture was stirred at room temperature for 3 h, then 1 mL of concentrated HCl was added and the mixture was stirred at 50° C., cooled to room temperature and 10 mL of ether was added. The mixture was cooled to −78° C., filtered; and the solid was washed with ether to yield 0.6 g of solid 70a as an HCl salt.

Workup

  1. stirringthe mixture was stirred at 50° C.
  2. temperaturecooled to room temperature
  3. temperatureThe mixture was cooled to −78° C.
  4. filtrationfiltered
  5. washand the solid was washed with ether

Sources & evidence

ORD record
ord-94c67941f7df40c4bad1b4d87dea91ac
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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