Trifluoroacetic acid → 2-Piperidin-4-yl-2,3-dihydro-isoindol-1-one trifluoroacetate

HRID 1715156Notes

Reaction equation

HRID 1715156 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:23])[CH2:10][CH2:9]1)=O)(C)(C)C.[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27]>ClCCl>[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27].[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:23])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11522569tert-Butyl 4-(1-oxoisoindolin-2-yl)piperidine-1-carboxylate

Product 1

HCID 685059012-Piperidin-4-yl-2,3-dihydro-isoindol-1-one trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.50 g, 1.58 mmol) in dichloromethane (15 mL) was added trifluoro-acetic acid (3.0 mL) and the reaction mixture stirred at ambient temperature during 4 h. The solvent was removed under reduced pressure and the crude product (0.710 g) used in the consecutive step without further purification assuming quantitative deprotection and formation of the trifluoroacetate salt. MS (ISP): 217.4 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product (0.710 g) used in the consecutive step without further purification

Sources & evidence

ORD record
ord-64f3a16e62e94645b1c9c07993d3c12b
Source dataset
uspto-grants-2010_09
Patent number
US07799806B2

Reaction notes

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