Acetonitrile → 5-(4-(2-Fluorophenoxymethyl)piperidino]methyl-2,4-dihydro-[1,2,4]triazol-3-one

HRID 914920Notes

Reaction equation

HRID 914920 reaction equation
Cl[CH2:2][C:3]1[NH:4][C:5](=[O:8])[NH:6][N:7]=1.Cl.[F:10][C:11]1[CH:24]=[CH:23][CH:22]=[CH:21][C:12]=1[O:13][CH2:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>C(OCC)(=O)C.O>[F:10][C:11]1[CH:24]=[CH:23][CH:22]=[CH:21][C:12]=1[O:13][CH2:14][CH:15]1[CH2:16][CH2:17][N:18]([CH2:2][C:3]2[NH:4][C:5](=[O:8])[NH:6][N:7]=2)[CH2:19][CH2:20]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 171780504-((2-Fluorophenoxy)methyl)piperidine hydrochlorideHCID 1355466853H-1,2,4-Triazol-3-one, 5-(chloromethyl)-1,2-dihydro-

Product 1

HCID 1355930115-(4-(2-Fluorophenoxymethyl)piperidino]methyl-2,4-dihydro-[1,2,4]triazol-3-oneYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 150 mg of 5-chloromethyl-2,4-dihydro-[1,2,4]triazol-3-one, 331 mg of 4-(2-fluorophenoxymethyl)piperidine hydrochloride and 180 mg of anhydrous potassium carbonate to acetonitrile, the mixture was stirred overnight at room temperature. Water and ethyl acetate were added to the reaction mixture and the insoluble portion was filtered out to obtain the title compound (70 mg, 21% yield).

Workup

  1. filtrationthe insoluble portion was filtered out

Sources & evidence

ORD record
ord-ecf08859a8864be1b28c37065c2a474d
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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