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Dimethylformamide → 2-[2-(4-Methylpiperazin-1-yl)ethoxy]-1-(1-naphthyl)-1-(tetrahydropyran-2-yloxy)ethane

HRID 976525
Notes
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Reaction equation

HRID 976525 reaction equation
[C:1]1([CH:11]([O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH2:12][O:13][CH2:14][CH2:15]OS(C2C=CC(C)=CC=2)(=O)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)C>[CH3:34][N:35]1[CH2:40][CH2:39][N:38]([CH2:15][CH2:14][O:13][CH2:12][CH:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH2:37][CH2:36]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 537184601(1-Naphthyl)-1-(tetrahydropyran-2yloxy)-2-[2(p-toluenesulfonyloxy)ethoxy]ethane

Product 1

HCID 536974332-[2-(4-Methylpiperazin-1-yl)ethoxy]-1-(1-naphthyl)-1-(tetrahydropyran-2-yloxy)ethane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 7.5 g of 1(1-naphthyl)-1-(tetrahydropyran-2yloxy)-2-[2(p-toluenesulfonyloxy)ethoxy]ethane, 2.65 ml of N-methylpiperazine, 3.96 g of potassium carbonate and 38 ml of N,N-dimethylformamide was stirred for 2 hours at 90°-100° C. The reaction mixture was cooled and added to a mixture of 100 ml of diethyl ether and 100 ml of ice water. The organic layer was separated. The aqueous layer was extracted twice each with 25 ml of diethyl ether. The extracts were 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 purified by column chromatography (eluant: chloroform/ethanol=10/1) to obtain 3.36 g of colorless, oily 2-[2-(4-methylpiperazin-1-yl)ethoxy]-1-(1-naphthyl)-1-(tetrahydropyran-2-yloxy)ethane (compound No. 258).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe organic layer was separated
  3. extractionThe aqueous layer was extracted twice each with 25 ml of diethyl ether
  4. washThe combined organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by column chromatography (eluant: chloroform/ethanol=10/1)

Sources & evidence

ORD record
ord-1ac71e27b62d41c8a0909bca56b6fea1
Source dataset
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05612381

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes