Potassium Carbonate → HCID 16061524, compound

HRID 1909691Notes

Reaction equation

HRID 1909691 reaction equation
Cl.[Cl:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[CH:21]=[CH:20][C:11]([O:12][CH2:13][C@@H:14]3[CH2:19][CH2:18][CH2:17][CH2:16][NH:15]3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.ClC[C:26]1[N:30]=[CH:29][O:28][N:27]=1.[C:31](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[CH:21]=[CH:20][C:11]([O:12][CH2:13][C@@H:14]3[CH2:19][CH2:18][CH2:17][CH2:16][N:15]3[CH2:31][C:29]3[O:28][N:27]=[CH:26][N:30]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27357653-(Chloromethyl)-1,2,4-oxadiazoleHCID 68996119HCID 68996119, compound

Product 1

HCID 16061524HCID 16061524, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-2-[4-(4-chloro-phenoxy)-phenoxymethyl]-piperidine hydrochloride (218 mg, 0.615 mmol), 3-(chloromethyl)-1,2,4-oxadiazole (47 mg, 0.393 mmol), and potassium carbonate (87 mg, 0.629 mmol) in DMF (2.5 mL) was heated for 18 h at rt. The solvent was removed in vacuo to obtain the crude mixture, which was purified by silica gel flash chromatography to obtain the title product (65 mg, 51%): MS; m/z 400 (M+H): LCMS (UV) 93%.

Workup

  1. customThe solvent was removed in vacuo
  2. customto obtain the crude mixture, which
  3. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-ef184cbc9c75487fba7271497f6dbc5a
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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