Ethanol → HCID 11338323, compound

HRID 1297490Notes

Reaction equation

HRID 1297490 reaction equation
[H-].[Na+].[CH3:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)[OH:12])=[CH:7][CH:6]=1.Cl.Cl[CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C(O)C>C1C=CC=CC=1>[N:27]1([CH2:26][CH2:25][O:12][CH:11]([C:8]2[CH:9]=[CH:10][C:5]([S:4][CH3:3])=[CH:6][CH:7]=2)[C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 11460188HCID 11460188, compound

Product 1

HCID 11338323HCID 11338323, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of sodium hydride (0.09 g, 3.84 mmol) in dry benzene (15 ml), (4-methylthiophenyl)-naphth-1-yl-carbinol (0.3 g, 1.07 mmol) was added. The contents were refluxed for 10 minutes and then N-[2-chloroethyl]-piperidine hydrochloride (0.4 g, 2.17 mmol) was added. The reaction mixture was refluxed for 24 hours and neutralized by ethyl alcohol and concentrated. The concentrate was extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous sodium sulfate and concentrated to give oil, which was purified by column chromatography on basic alumina by using benzene-hexane as eluent to yield the desired product.

Workup

  1. additionwas added
  2. temperatureThe contents were refluxed for 10 minutes
  3. temperatureThe reaction mixture was refluxed for 24 hours
  4. concentrationconcentrated
  5. extractionThe concentrate was extracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customto give oil, which
  11. customwas purified by column chromatography on basic alumina

Sources & evidence

ORD record
ord-dccf898a495941768cdadcefae4ca410
Source dataset
uspto-grants-2007_07
Patent number
US07250446B2

Reaction notes

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