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

HRID 1044822Notes

Reaction equation

HRID 1044822 reaction equation
[ClH:1].[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[O:13][CH:14]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]1>O1CCOCC1>[ClH:1].[NH:17]1[CH2:18][CH2:19][CH:14]([O:13][N:4]2[C:3](=[O:2])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]2=[O:12])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21751544Tert-butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylate

Product 1

HCID 217515372-(Piperidin-4-yloxy)isoindoline-1,3-dione hydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Hydrogen chloride in 1,4-dioxane (4 M, 7.0 ml) was added to the solution of tert-butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylate (692 mg, 2.00 mmol) in 1,4-dioxane (4 ml) and stirred for 1 hour. The precipitated material was collected, washed with n-hexane (2 ml×2) and dried under reduced pressure at 80° C. to give 2-(piperidin-4-yloxy)isoindoline-1,3-dione hydrochloride (533 mg, 94%).

Workup

  1. customThe precipitated material was collected
  2. washwashed with n-hexane (2 ml×2)
  3. customdried under reduced pressure at 80° C.

Sources & evidence

ORD record
ord-b65009fc1ee84c54a9849eb13aa5e6a9
Source dataset
uspto-grants-2013_10
Patent number
US08563732B2

Reaction notes

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