Sodium Hydroxide → HCID 13671866, compound

HRID 1655325Notes

Reaction equation

HRID 1655325 reaction equation
[NH2:1][CH:2]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[ClH:16].S(C1C=CC(C)=CC=1)(O[CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)(=O)=O.C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(O)C.O.CCOCC>[ClH:16].[ClH:16].[CH3:14][CH:13]([CH3:15])[CH2:12][CH2:11][CH:2]([NH:1][CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 13671865HCID 13671865, compoundHCID 19791697HCID 19791697, compound

Product 1

HCID 13671866HCID 13671866, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of (1RS,2SR)-2-amino-5-methyl-1-phenylhexan-1-ol (1.04 g, 5 mmol), 3-piperidinopropyl tosylate hydrochloride (2.00 g, 6 mmol) and sodium bicarbonate (1.05 g, 12.5 mmol) in ethanol (10 ml) was refluxed for 1 hour. After cooling, to the reaction mixture were added ether (100 ml), water (50 ml) and 2N-NaOH (5 ml) and the resulting mixture was well shaken. The ethereal layer was separated and washed three times with water, then once with brine, followed by drying and subsequent concentration under reduced pressure. The residue was dissolved in ethanol and to the solution was added 6N-HCl in EtOH (1.5 ml). Precipitated crystals were collected by filtration and then recrystallized from ethanol to obtain 0.73 g of the title compound as white crystals (yield: 36%).

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling, to the reaction mixture
  3. customThe ethereal layer was separated
  4. washwashed three times with water
  5. customby drying
  6. concentrationsubsequent concentration under reduced pressure
  7. dissolutionThe residue was dissolved in ethanol and to the solution
  8. additionwas added 6N-HCl in EtOH (1.5 ml)
  9. customPrecipitated crystals
  10. filtrationwere collected by filtration
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-985c44c167284781af9b5eb92d5754d8
Source dataset
uspto-grants-1993_10
Patent number
US05250546

Reaction notes

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