3-(2-Ethylpiperidin-1-yl)propan-1-amine → 4-(5-methyl-2-phenyl-4,5,6,7-tetrahydro-1H-indol-1-yl)benzoic acid

HRID 2064565Notes

Reaction equation

HRID 2064565 reaction equation
[C:1]1([C:7]2[N:8]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=3[CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:25](C1CCCCN1CCCN)C>>[CH3:25][CH:12]1[CH2:11][CH2:10][C:9]2[N:8]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:23][CH:24]=3)[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:15][C:14]=2[CH2:13]1

Participants

3

Reactant 2

HCID 41174793-(2-Ethylpiperidin-1-yl)propan-1-amineHCID 66233704-(2-phenyl-4,5,6,7-tetrahydro-1H-indol-1-yl)benzoic acid2×

Product 1

HCID 208875554-(5-methyl-2-phenyl-4,5,6,7-tetrahydro-1H-indol-1-yl)benzoic acidYield 62%

Procedure

Following the general methods as outlined under Example 1, starting from 4-(2-phenyl-4,5,6,7-tetrahydro-1H-indol-1-yl)benzoic acid (Intermediate 7) and 3-(2-ethylpiperidin-1-yl)propan-1-amine, the title compound (8) was isolated as a beige solid in 62% yield (94% purity by HPLC). MS(ESI+): 470.8; MS(ESI−): 468.7.

Sources & evidence

ORD record
ord-4995467ed6ca4472a3e41b1257ee8488
Source dataset
uspto-grants-2012_10
Patent number
US08288432B2

Reaction notes

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