Piperidin-4-ol → 1-[2-Hydroxy-2-(5-phenyl-1,2-oxazol-3-yl)ethyl]piperidin-4-ol

HRID 1580050Notes

Reaction equation

HRID 1580050 reaction equation
[OH:1][CH:2]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:7][N:6]=1)[CH2:3]Br.[OH:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])O.[Na+]>C(O)C.C1C=CC=CC=1>[OH:1][CH:2]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:7][N:6]=1)[CH2:3][N:20]1[CH2:21][CH2:22][CH:17]([OH:16])[CH2:18][CH2:19]1

Participants

6

Reactant 3

HCID 79341Piperidin-4-olHCID 516892Sodium BicarbonateHCID 21796578HCID 21796578, compound

Product 1

HCID 30434821-[2-Hydroxy-2-(5-phenyl-1,2-oxazol-3-yl)ethyl]piperidin-4-olYield 62.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(1-hydroxy-2-bromoethyl)-5-phenylisoxazole (268 mg) and 4-hydroxypiperidine (121 mg) is dissolved in a mixture (4 ml) of 99% ethanol and benzene (1:1). To the solution is added sodium hydrogen carbonate (168 mg) and stirred at 70°C for 5 hours. After removal of the solvent, the residue is subjected to a column chromatography (silica gel,) eluted with a mixture of methylene chloride and methanol, and the crude crystals collected are recrystallized from ethyl acetate to give 3-[1-hydroxy-2-(4-hydroxypiperidino)ethyl]-5-phenylisoxazole (180 mg) as colorless prisms melting at 117-119°C.

Workup

  1. customAfter removal of the solvent
  2. washeluted with a mixture of methylene chloride and methanol
  3. customthe crude crystals collected
  4. customare recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d54391f64e1b4983a4da942539267a49
Source dataset
uspto-grants-1976_01
Patent number
US03932426

Reaction notes

Loading…