Potassium Carbonate → tert-Butyl 4-(3-(4-chlorophenyl)-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate

HRID 222239Notes

Reaction equation

[NH:1]([C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=O)[NH2:2].[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]2[N:24]=[C:3]([CH:5]3[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]3)[NH:1][N:2]=2)=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate (1.0 g), 4-chlorobenzonitrile (1.7 g), potassium carbonate (0.28 g), and butanol (8.0 mL) was heated at 150° C. for 2 hours using a microwave device. After leaving to be cooled, the solvent was evaporated under reduced pressure, and the residue was azeotroped with toluene. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 90/10). To the purified product was added diisopropyl ether, and the resulting solid was collected by filtration and dried under reduced pressure to obtain tert-butyl 4-[3-(4-chlorophenyl)-1H-1,2,4-triazol-5-yl]piperidine-1-carboxylate (0.62 g).

Workup

customAfter leaving
temperatureto be cooled
customthe solvent was evaporated under reduced pressure
customthe residue was azeotroped with toluene
customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 90/10)
additionTo the purified product was added diisopropyl ether
filtrationthe resulting solid was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-20aa3d480e3f49af80839ad9994e8f33
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207199B2

Reaction notes

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