Benzaldehyde → 2-{[3-(2-Amino-ethyl)-6-ethyl-1H-indol-2-yl]-phenyl-methyl}-3-hydroxy-4-phenyl-cyclopent-2-enone

HRID 1432488Notes

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:32]=[C:31]2[C:27]([C:28]([CH2:33][CH2:34][NH2:35])=[CH:29][NH:30]2)=[CH:26][CH:25]=1)[CH3:23]>>[NH2:35][CH2:34][CH2:33][C:28]1[C:27]2[C:31](=[CH:32][C:24]([CH2:22][CH3:23])=[CH:25][CH:26]=2)[NH:30][C:29]=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 690696643-Hydroxy-4-phenyl-cyclopent-2-enone

HCID 690700642-(6-ethyl-1H-indol-3-yl)-ethylamine

Product 1

HCID 579334452-{[3-(2-Amino-ethyl)-6-ethyl-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-(6-ethyl-1H-indol-3-yl)-ethylamine (Lit. 8) to give the title compound as a pale brown solid. MS: 451.0 ([M+H]+).

Sources & evidence

ORD record: ord-64249a88e9c649b5a4d6ea15e32a0173
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612099B2

Reaction notes

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