Ethanol hydrochloride → 1-(1H-inden-6-yl)-2-[2-(N,N-dimethylamino)ethoxy]ethanol hydrochloride
Reaction equation
C([O:4][CH:5]([C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[CH:18][CH2:19]2)=[CH:15][CH:14]=1)[CH2:6][O:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])(=O)C.C[O-].[Na+].CO.[ClH:27].C(O)C>CO.C(O)C>[ClH:27].[CH2:19]1[C:20]2[C:16](=[CH:15][CH:14]=[C:13]([CH:5]([OH:4])[CH2:6][O:7][CH2:8][CH2:9][N:10]([CH3:11])[CH3:12])[CH:21]=2)[CH:17]=[CH:18]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
In 0.5 ml of methanol was dissolved 80 mg of 1-acetoxy-1-(1H-inden-6-yl)-2-[2-(N,N-dimethylamino)ethoxy]ethane. To the solution was added 80 mg of a 28% sodium methoxide-methanol solution with ice cooling. The resulting mixture was stirred at room temperature for 20 minutes. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: chloroform/methanol=20/1) to obtain a yellow oily product. The oily product was dissolved in 0.1 ml of ethanol. To the solution was added 0.1 ml of a 5.9N dry hydrogen chloride-ethanol solution at room temperature. The resulting crystals were collected by filtration to obtain 20 mg of 1-(1H-inden-6-yl)-2-[2-(N,N-dimethylamino)ethoxy]ethanol hydrochloride (compound No. 298).
Workup
- customThe solvent was removed by distillation under reduced pressure
- customThe residue thus obtained
- customwas purified by column chromatography (eluant: chloroform/methanol=20/1)
- customto obtain a yellow oily product
- filtrationThe resulting crystals were collected by filtration
Sources & evidence
- ORD record
- ord-cc5d7d2f22364c01b188552e799b9631
- Source dataset
- uspto-grants-1995_12
- Patent number
- US05472984
Reaction notes
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