Potassium Carbonate → HCID 3079387, compound

HRID 1651553Notes

Reaction equation

HRID 1651553 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][NH2:18])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.Cl[C:26]1[O:27][C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[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][NH:18][C:26]3[O:27][C:28]4[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=4[N:30]=3)[CH2:12][CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119862-ChlorobenzoxazoleHCID 15055857HCID 15055857, compound

Product 1

HCID 3079387HCID 3079387, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 1.12 g (3.24 mmol) of 2-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]ethylamine obtained in Example 12 and 0.60 g (3.91 mmol) of 2-chlorobenzoxazole were added 0.57 g (4.12 mmol) of potassium carbonate and 5 ml of dioxane, and the mixture was stirred under heating at an oil-bath temperature of 80° to 85° C. for 3 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 chloroform as an eluent, and the desired fraction was concentrated under reduced pressure to give 0.72 g (48%) of 2-[2-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]ethylamino]benzoxazole as an oil.

Workup

  1. temperatureunder heating at an oil-bath temperature of 80° to 85° C. for 3 hours
  2. customAfter the reaction
  3. filtrationthe insolubles were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was separated by silica gel column chromatography
  6. concentrationthe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-790b551da4ea4720857c1ef2e347ecad
Source dataset
uspto-grants-1990_05
Patent number
US04929618

Reaction notes

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