Trifluoroacetic acid → Trifluoroacetic acid

HRID 2112554Notes

Reaction equation

HRID 2112554 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([N:15]1[CH2:20][CH2:19][C:18]([CH2:22][N:23]2[C:31](=[O:32])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]2=[O:33])([F:21])[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:21][C:18]1([CH2:22][N:23]2[C:24](=[O:33])[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:31]2=[O:32])[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53415317Tert-butyl 4-((1,3-dioxoisoindolin-2-yl)methyl)-4-fluoropiperidine-1-carboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 230692652-(4-Fluoro-piperidin-4-ylmethyl)-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (30 ml) was added to a solution of 4-[(1,3-dioxoisoindolin-2-yl)methyl]-4-fluoropiperidinecarboxylic acid tert-butyl ester (23 g) in dichloromethane (250 ml), and the mixture was stirred at room temperature for 5 hours. The obtained solution was concentrated, and the residue was recrystallized from ether to obtain a trifluoroacetic acid salt of 2-(4-fluoro-piperidin-4-ylmethyl)-isoindole-1,3-dione.

Workup

  1. concentrationThe obtained solution was concentrated
  2. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-4e3674a234174d2395b9bad9a0cb987f
Source dataset
uspto-grants-2009_04
Patent number
US07524841B2

Reaction notes

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