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Acetic Anhydride → 1-acetoxy-1-(6-benzyloxy-2-naphthyl)-2-[2-(N,N-dimethylamino)ethoxy]ethane hydrochloride

HRID 862529
Notes
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Reaction equation

HRID 862529 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH:19]([OH:27])[CH2:20][O:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+].[ClH:41].C(O)C>N1C=CC=CC=1.CC(C)=O.O.C(OCC)(=O)C>[ClH:41].[C:28]([O:27][CH:19]([C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=2)[CH:15]=1)[CH2:20][O:21][CH2:22][CH2:23][N:24]([CH3:25])[CH3:26])(=[O:30])[CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 21887872Ethanol hydrochlorideHCID 544081981-(6-benzyloxy-2-naphthyl)-2-[2-(N,N-dimethylamino)ethoxy]ethanol

Product 1

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

Reagents, catalysts & solvents 4

HCID 180AcetoneSolvent
HCID 962WaterSolvent
HCID 1049PyridineSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

In 12 ml of pyridine was suspended 3.0 g of 1-(6-benzyloxy-2-naphthyl)-2-[2-(N,N-dimethylamino)-ethoxy]ethanol. To the suspension was added 1.6 ml of acetic anhydride. The resulting mixture was stirred at room temperature for 24 hours. After the completion of the reaction, the solvent was removed by distillation under reduced pressure. To the residue thus obtained were added 60 ml of ethyl acetate and 60 ml of water. The mixture was adjusted to pH 10.5 with potassium carbonate. The organic layer was separated. The aqueous layer was extracted with 30 ml of ethyl acetate. The extract was combined with the previously separated organic layer. The combined organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was dissolved in 30 ml of acetone. To the solution was added 1.5 ml of a 5N dry hydrogen chloride-ethanol solution. The resulting mixture was stirred at room temperature for 1 hour. The resulting crystals were collected by filtration and dried to obtain 2.6 g of 1-acetoxy-1-(6-benzyloxy-2-naphthyl)-2-[2-(N,N-dimethylamino)ethoxy]ethane hydrochloride (compound No. 286).

Workup

  1. customAfter the completion of the reaction
  2. customthe solvent was removed by distillation under reduced pressure
  3. customTo the residue thus obtained
  4. customThe organic layer was separated
  5. extractionThe aqueous layer was extracted with 30 ml of ethyl acetate
  6. washThe combined organic layer was washed with water
  7. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customThe residue thus obtained
  10. stirringThe resulting mixture was stirred at room temperature for 1 hour
  11. filtrationThe resulting crystals were collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-7c92a1550974419485fb756e4bfbce5d
Source dataset
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05719150

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes