Benzaldehyde → 2-{[3-(2-Amino-ethyl)-5-methyl-1H-indol-2-yl]-phenyl-methyl}-3-hydroxy-4-phenyl-cyclopent-2-enone

HRID 1432486Notes

Reaction equation

[OH:1][C:2]1[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][C:4](=[O:13])[CH:3]=1.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:22]([C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][CH:28]=[C:27]2[CH2:33][CH2:34][NH2:35])C>>[NH2:35][CH2:34][CH2:33][C:27]1[C:26]2[C:30](=[CH:31][CH:32]=[C:24]([CH3:22])[CH:25]=2)[NH:29][C:28]=1[CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]1[C:4](=[O:13])[CH2:5][CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:2]=1[OH:1]

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 1880061H-Indole-3-ethanamine, 5-ethyl-

HCID 690696643-Hydroxy-4-phenyl-cyclopent-2-enone

Product 1

HCID 579334082-{[3-(2-Amino-ethyl)-5-methyl-1H-indol-2-yl]-phenyl-methyl}-3-hydroxy-4-phenyl-cyclopent-2-enone

Procedure

Using general procedure C, 3-hydroxy-4-phenyl-cyclopent-2-enone (Lit. 17) was reacted with benzaldehyde and 2-(5-ethyl-1H-indol-3-yl)-ethylamine to give the title compound as orange solid. MS: 437.1 ([M+H]+).

Sources & evidence

ORD record: ord-4d4e091a14d5406c9c8c8f1fba2b8398
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612099B2

Reaction notes

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