Ethanol, 1-bromo- → 2-[4-(2-hydroxyethyl)piperazin-1-yl]-1-phenyl-1H-indole-3-carboxaldehyde

HRID 751380Notes

Reaction equation

HRID 751380 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH:16]=[O:17])=[C:8]2[N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:25]([OH:27])[CH3:26]>>[OH:27][CH2:25][CH2:26][N:21]1[CH2:22][CH2:23][N:18]([C:8]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:15]3[C:10]([C:9]=2[CH:16]=[O:17])=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 14202443Ethanol, 1-bromo-HCID 539968311-Phenyl-2-piperazin-1-yl-1H-indole-3-carboxaldehyde

Product 1

HCID 111755082-[4-(2-hydroxyethyl)piperazin-1-yl]-1-phenyl-1H-indole-3-carboxaldehydeYield 87%

Procedure

1-Phenyl-2-piperazin-1-yl-1H-indole-3-carboxaldehyde is reacted with bromoethanol as described in Example 30 to afford 2-[4-(2-hydroxyethyl)piperazin-1-yl]-1-phenyl-1H-indole-3-carboxaldehyde (87% yield) as a yellow solid. TLC (ethyl acetate-10% methanol) Rf 0.13; ESI/MS 350 (M+H); RT 2.67 min; NMR 10.16 (1H, s); 8.13 (1H, d, J=6 Hz); 7.68 (5H, m); 7.20 (2H, m); 6.91 (1H, d, J=6 Hz); 4.39 (1H, t); 3.47 (2H, q); 3.2 (4H, m); 2.34 (6H, m).

Sources & evidence

ORD record
ord-482b6c167d574f1f96e166b753a3abba
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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