Trifluoroacetic acid → 2-(Piperidin-4-yloxy)isoindoline-1,3-dione trifluoroacetic acid

HRID 1895898Notes

Reaction equation

HRID 1895898 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[O:12][CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1.[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29]>>[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].[NH:16]1[CH2:17][CH2:18][CH:13]([O:12][N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])[CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21751544Tert-butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylate

Product 1

HCID 671183852-(Piperidin-4-yloxy)isoindoline-1,3-dione trifluoroacetic acidYield 90%

Procedure

tert-Butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylate (3.81 g, 11.0 mmol) was added to trifluoroacetic acid (80 ml) and the mixture was stirred at room temperature for 30 minutes. The reaction was concentrated in vacuo and the residue was triturated with diethyl ether (100 ml). The resulting solid was washed with diethyl ether (20 ml×3) to give 2-(piperidin-4-yloxy)isoindoline-1,3-dione trifluoroacetic acid (3.50 g, 90%) as a white solid: LCMS: 247 [M+1]+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue was triturated with diethyl ether (100 ml)
  3. washThe resulting solid was washed with diethyl ether (20 ml×3)

Sources & evidence

ORD record
ord-168fafd5c86d428fb1c805279023fa9a
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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