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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

HRID 1198259
Notes
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Reaction equation

HRID 1198259 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 675979821-acetoxy-1-(6-benzyloxy-2-naphthyl)-2-[2-(N,N-dimethylamino)ethoxy]ethane hydrochloride

Product 1

HCID 675970851-acetoxy-1-(6-hydroxy-2-naphthyl)-2-[2-(N,N-dimethylamino)ethoxy]ethane hydrochlorideYield 47.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

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

  1. customwas subjected to hydrogenation at room temperature under atmospheric pressure
  2. customAfter the completion of the reaction
  3. customthe palladium-carbon was removed by filtration
  4. customThe solvent was removed by distillation under reduced pressure
  5. additionAcetone was added to the residue
  6. customthus obtained
  7. filtrationThe resulting crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-3862ec23ea6946828e3a51f3c1b67f3b
Source dataset
uspto-grants-1994_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05280032

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes