Maleic Anhydride → (1S)-2-(1-Cyclohexylpiperidin-4-yl)-1-methyl-3-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid

HRID 1618115Notes

Reaction equation

[CH:1]1([N:7]2[CH2:12][CH2:11][CH:10]([NH:13][C@H:14]([C:16]3O[CH:18]=[CH:19][CH:20]=3)[CH3:15])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:21]1(=[O:27])[O:26][C:24](=[O:25])[CH:23]=[CH:22]1>C1(C)C=CC=CC=1>[CH:1]1([N:7]2[CH2:8][CH2:9][CH:10]([N:13]3[C:24](=[O:25])[C:23]4[C:22]([C:21]([OH:26])=[O:27])=[CH:18][CH:19]=[CH:20][C:16]=4[C@@H:14]3[CH3:15])[CH2:11][CH2:12]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

1-Cyclohexyl-N-[(1S)-1-(furan-2-yl)ethyl]piperidin-4-amine (0.3 gr, 1.08 mmol) and maleic anhydride (0.13 gr, 1.3 mmol) in toluene (10 mL) were stirred at reflux for 16 hours. Solvent was evaporated and the residue was dissolved in aqueous 37% hydrochloric acid (5 mL) and stirred at 100° C. for 2 hours. Volatiles were evaporated affording crude title product that was used for the next step without further purification

Workup

temperatureat reflux for 16 hours
customSolvent was evaporated
dissolutionthe residue was dissolved in aqueous 37% hydrochloric acid (5 mL)
customVolatiles were evaporated

Sources & evidence

ORD record: ord-f579d8ef94394998baa2c9e63caaeb02
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765972B2

Reaction notes

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