1-acetoxy-1-(6-benzyloxy-2-naphthyl)-2-[2-(N,N-dimethylamino)ethoxy]ethane hydrochloride → 1-acetoxy-1-(6-hydroxy-2-naphthyl)-2-[2-(N,N-dimethylamino)ethoxy]ethane hydrochloride
Reaction equation
[ClH:1].[C:2]([O:5][CH:6]([C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:24]CC3C=CC=CC=3)[CH:20]=2)[CH:15]=1)[CH2:7][O:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])(=[O:4])[CH3:3]>[C].[Pd].C(O)C>[ClH:1].[C:2]([O:5][CH:6]([C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:24])[CH:20]=2)[CH:15]=1)[CH2:7][O:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])(=[O:4])[CH3:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 2.0 g of 1-acetoxy-1-(6-benzyloxy-2-naphthyl)-2-[2-(N,N-dimethylamino)ethoxy]ethane hydrochloride, 0.5 g of 5% palladium-carbon and 40 ml of ethanol was subjected to hydrogenation at room temperature under atmospheric pressure. After the completion of the reaction, the palladium-carbon was removed by filtration. The solvent was removed by distillation under reduced pressure. Acetone was added to the residue thus obtained. The resulting crystals were collected by filtration and dried to obtain 0.76 g of 1-acetoxy-1-[6-hydroxy-2-naphthyl)-2-(2-(N,N-dimethylamino)ethoxy]ethane hydrochloride (compound No. 287).
Workup
- customwas subjected to hydrogenation at room temperature under atmospheric pressure
- customAfter the completion of the reaction
- customthe palladium-carbon was removed by filtration
- customThe solvent was removed by distillation under reduced pressure
- additionAcetone was added to the residue
- customthus obtained
- filtrationThe resulting crystals were collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-497bd478b40c4f4eaf438cadf1258303
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05872117
Reaction notes
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