2-Chlorobenzoxazole → 2-[2-[4-[(4-Chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]ethoxy]benzoxazole

HRID 1651551Notes

Reaction equation

HRID 1651551 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][OH:18])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:28]1[O:29][C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][O:18][C:28]3[O:29][C:30]4[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=4[N:32]=3)[CH2:12][CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 119862-ChlorobenzoxazoleHCID 24758Sodium hydrideHCID 150558552-[4-[(4-Chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]ethanol

Product 1

HCID 150558562-[2-[4-[(4-Chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]ethoxy]benzoxazoleYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2.35 g (6.78 mmol) of 2-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1piperidyl]ethanol obtained in Example 10 dissolved in 20 ml of toluene was added 0.53 g (13.25 mmol) of sodium hydride (60% dispersion in mineral oil), and 1.25 g (8.14 mmol) of 2-chlorobenzoxazole was added to the mixed solution. The mixture stirred under reflux for 7 hours. After the reaction, the insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The residue was separated by silica gel column chromatography using a mixture of chloroform and methanol in the volume ratio of 40:1 as the developing solvent. The desired fractions was concentrated under reduced pressure to give 1.10 g (35%) of 2-[2-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]ethoxy]benzoxazole as an oil.

Workup

  1. additionwas added to the mixed solution
  2. temperatureunder reflux for 7 hours
  3. customAfter the reaction
  4. filtrationthe insolubles were filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was separated by silica gel column chromatography
  7. additiona mixture of chloroform and methanol in the volume ratio of 40:1 as the developing solvent
  8. concentrationThe desired fractions was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f98f097c4977470b94f3d9d5d80acb72
Source dataset
uspto-grants-1990_05
Patent number
US04929618

Reaction notes

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