Hydrochloric Acid → 3-[3-(carboxymethylthio)propyl]-N-(3-pyridyl)indole hydrochloride
Reaction equation
C([O:3][C:4]([CH2:6][S:7][CH2:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=1)=[O:5])C.[ClH:26]>CO.[OH-].[Na+].CC(C)=O>[ClH:26].[C:4]([CH2:6][S:7][CH2:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=1)([OH:5])=[O:3]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of 90 mg of 3-[3-(ethoxycarbonylmethylthio)propyl]-N-(3-pyridyl)indole in 5 ml of methanol and 1 ml of 1N sodium hydroxide is refluxed for 10 hours, cooled and evaporated. The resulting oil is partitioned between ether and water. The aqueous phase is brought to pH=6 with concentrated sulfuric acid, is extracted with chloroform and the chloroform extract is dried over sodium sulfate. Filtration and evaporation gives an oil which is redissolved in 2 ml of acetone and is treated with 0.07 ml of 3N ethereal hydrogen chloride. Evaporation and crystallization from acetone-ether yields 3-[3-(carboxymethylthio)propyl]-N-(3-pyridyl)indole hydrochloride, m.p. 106°-110°.
Workup
- temperaturecooled
- customevaporated
- customThe resulting oil is partitioned between ether and water
- extractionis extracted with chloroform
- extractionthe chloroform extract
- dry with materialis dried over sodium sulfate
- filtrationFiltration and evaporation
- customgives an oil which
- customEvaporation and crystallization from acetone-ether
Sources & evidence
- ORD record
- ord-fdbfe043bd204a7686892102162c328f
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04536505
Reaction notes
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