Hydrochloric Acid → 2-[4-(2-hydroxyethyl)piperazin-1-yl]-1-phenyl-1H-indole-3-carboxaldehyde hydrochloride

HRID 1678164Notes

Reaction equation

HRID 1678164 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]3[C:17]([C:18]=2[CH:19]=[O:20])=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:6][CH2:5]1.[ClH:27]>CO>[ClH:27].[OH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]3[C:17]([C:18]=2[CH:19]=[O:20])=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 111755082-[4-(2-hydroxyethyl)piperazin-1-yl]-1-phenyl-1H-indole-3-carboxaldehyde

Product 1

HCID 114519692-[4-(2-hydroxyethyl)piperazin-1-yl]-1-phenyl-1H-indole-3-carboxaldehyde hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[4-(2-Hydroxyethyl)piperazin-1-yl]-1-phenyl-1H-indole-3-carboxaldehyde is dissolved in methanol and treated with 1M ethereal hydrochloric acid. After stirring for 30 min., the solvent is removed and the residue is dissolved in a small amount of methanol and treated with ether to precipitate 2-[4-(2-hydroxyethyl)piperazin-1-yl]-1-phenyl-1H -indole-3-carboxaldehyde hydrochloride (85% yield) as a cream solid. ESI/MS 350 (M+H); RT=2.32 min; NMR 10.15 (1H, s); 8.13 (1H, d, 9 Hz); 7.70 (5H, m); 7.25 (2H, m); 6.96 (1H, d, J=6 Hz); 5.31 (1H, br s); 3.73 (2H, br s); 3.56 (6H, br m); 3.17 (2H, br s); 2.97 (2H, br s).

Workup

  1. customthe solvent is removed
  2. dissolutionthe residue is dissolved in a small amount of methanol
  3. additiontreated with ether

Sources & evidence

ORD record
ord-ab453b254d7b449fa3466db92719530c
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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