Piperidine → 2-Oxo-3-[5-(3-pyrrolidin-1-yl-propyl)-1H-indol-2-ylmethylene]-2,3-dihydro-1H-indole-5-carboxylic acid

HRID 1790931Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)([OH:3])=[O:2].[N:14]1([CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][C:26]([CH:31]=O)=[CH:25]3)[CH2:18][CH2:17][CH2:16][CH2:15]1.N1CCCCC1>C(O)C>[O:13]=[C:8]1[C:7](=[CH:31][C:26]2[NH:27][C:28]3[C:24]([CH:25]=2)=[CH:23][C:22]([CH2:21][CH2:20][CH2:19][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:30][CH:29]=3)[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([C:1]([OH:3])=[O:2])[CH:5]=2)[NH:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-carboxy-2-oxindole (35 mg, 0.2 mmol), 5-(3-pyrrolidin-1-yl-propyl)-1H-indole-2-carbaldehyde (51 mg, 0.2 mmol) and piperidine (0.2 mL) in ethanol (1 mL) was heated in a sealed tube at 80° C. for 6 hours. The reaction mixture was concentrated and the residue was dissolved in methanol, made acidic with 1 N hydrochloric acid until solid was formed. The precipitate was filtered, washed with 1 N hydrochloric acid, water, ethanol and dried to give the title compound.

Workup

concentrationThe reaction mixture was concentrated
dissolutionthe residue was dissolved in methanol
customwas formed
filtrationThe precipitate was filtered
washwashed with 1 N hydrochloric acid, water, ethanol
customdried

Sources & evidence

ORD record: ord-c550b8fc70904b66b7a429d15322bdd5
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071332B2

Reaction notes

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