Piperidine → (E)-3-(5-Nitroindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one

HRID 618104

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[N+:16]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH:28]=O)([O-:18])=[O:17].N1CCCCC1>CN(C)C=O>[N+:16]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2/[CH:28]=[CH:14]/[C:13]([C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:15])([O-:18])=[O:17]

Participants

Conditions

Temperature: 100 °C

Procedure

3',4',5'-Trimethoxyacetophenone (1.31 g) and 5-nitroindole-3-carboxaldehyde (1.18 g) were dissolved in N,N-dimethylformamide (20 ml), and piperidine (528.7 mg) was added thereto, followed by stirring at 100° C. for 72 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from methanol to give Compound 21 (125 mg).

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography
customThe obtained crude crystals
customwere recrystallized from methanol

Sources & evidence

ORD record: ord-e5fc7ad1fae14f72a4885117db483730
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05952355

Linked notes

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