Hydrochloric Acid → HCID 67854283, compound

HRID 1655326Notes

Reaction equation

HRID 1655326 reaction equation
[CH3:1][CH:2]([CH3:24])[CH2:3][CH2:4][CH:5]([NH:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[OH:7].[H-].[Na+].S(C1C=CC(C)=CC=1)(O[CH3:31])(=O)=O.[ClH:39]>C1(C)C=CC=CC=1.CC(C)=O>[ClH:39].[ClH:39].[CH3:31][O:7][CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:5]([NH:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[CH2:4][CH2:3][CH:2]([CH3:24])[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6645Methyl p-toluenesulfonateHCID 24758Sodium hydrideHCID 1283085-Methyl-1-phenyl-2-{[3-(piperidin-1-yl)propyl]amino}hexan-1-ol

Product 1

HCID 67854283HCID 67854283, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

To a solution of (1RS,2SR)-5-methyl-1-phenyl-2-(3-piperidinopropylamino)hexan-1-ol (1.66 g, 5 mmol) in toluene (25 ml) was added sodium hydride (0.14 g, 6 mmol) and the mixture was refluxed for 1 hour. To the reaction mixture was added methyl tosylate (1.12 g, 6 mmol) and the resulting mixture was refluxed for further 1 hour. After being cooled, the mixture was washed twice with water and once with brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by neutral alumina column chromatography (alumina: 40 g, eluent: chloroform) to give 1.1 g of oily matter. To a solution of the matter in acetone (20 ml) was added concentrated hydrochloric acid (0.1 ml) and the mixture was concentrated under reduced pressure. The residue was recrystallized from acetone (10 ml)-ethanol (0.2 ml) to obtain 0.45 g of the title compound as white crystals (yield: 21%).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperaturethe resulting mixture was refluxed for further 1 hour
  3. temperatureAfter being cooled
  4. washthe mixture was washed twice with water and once with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by neutral alumina column chromatography (alumina: 40 g, eluent: chloroform)
  8. customto give 1.1 g of oily matter
  9. concentrationthe mixture was concentrated under reduced pressure
  10. customThe residue was recrystallized from acetone (10 ml)-ethanol (0.2 ml)

Sources & evidence

ORD record
ord-aabc9d85e47e46cba8039f597fdfbfe0
Source dataset
uspto-grants-1993_10
Patent number
US05250546

Reaction notes

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