Benzylamine → 4-(4-Benzyl-5-methyl-4H-[1,2,4]triazol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 6914Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2O[C:16]([CH3:19])=[N:17][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>[Cl-].[Mg+2].[Cl-]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:27]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:16]([CH3:19])=[N:17][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

4-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (5 g, 18.7 mmol) (see reference WO 0039125), benzylamine (2.5 ml, 22 mmol) and magnesium chloride (100 mg) were heated at 150° C. for 1 hour, a further quantity of benzylamine (2.5 ml, 22 mmol) was added and the mixture was heated at 150° C. for 4 hours. The reaction mixture was cooled to room temperature and the reaction mixture was purified by chromatography on silica gel using methanol in dichloromethane as eluant (3:97). The material isolated was triturated with diethyl ether to give the title compound as a white solid (4.69 g).

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe reaction mixture was purified by chromatography on silica gel
customThe material isolated
customwas triturated with diethyl ether

Sources & evidence

ORD record: ord-f6db3128a3104baab6ac26020f6aaa80
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084145B2

Reaction notes

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