Ammonia → HCID 23285164, compound

HRID 369191Notes

Reaction equation

[NH3:1].[CH3:2][N:3]([CH:16]1[CH2:21][CH2:20][N:19]([C:22](=[O:34])[C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH:33]=[N:32][CH:31]=[N:30]3)=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](OC)=[O:13])=[CH:8][CH:7]=1>CO>[CH3:2][N:3]([CH:16]1[CH2:21][CH2:20][N:19]([C:22](=[O:34])[C:23]2[CH:24]=[CH:25][C:26]([N:29]3[CH:33]=[N:32][CH:31]=[N:30]3)=[CH:27][CH:28]=2)[CH2:18][CH2:17]1)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:13])[NH2:1])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

45 ml of a saturated solution of ammonia in methanol was added to 600 mg of 4-{N-methyl-N-[2-(4-methoxycarbonylphenyl)ethyl]amino}-1-[4-(1,2,4-triazol-1-yl)benzoyl]piperidine. The mixture was stirred at 110° C. for 69.5 hours in a sealed tube. The reaction mixture was cooled to room temperature and then subjected to distillation to remove the solvent. The residue was purified by a silica gel column chromatography (eluant: dichloromethane/methanol/ammonia water=200/20/1). The product was washed with diethyl ether for crystallization, followed by recrystallization from ethanol to obtain 320 mg of 4-{N-methyl-N-[2-(4-carbamoylphenyl)ethyl]amino}-1-[4-(1,2,4-triazol-1-yl)benzoyl]piperidine as a white powder.

Workup

temperatureThe reaction mixture was cooled to room temperature
distillationsubjected to distillation
customto remove the solvent
customThe residue was purified by a silica gel column chromatography (eluant: dichloromethane/methanol/ammonia water=200/20/1)
washThe product was washed with diethyl ether for crystallization
customfollowed by recrystallization from ethanol

Sources & evidence

ORD record: ord-7e7e88ec8203486d83dccf91c9c1b3b9
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136826

Reaction notes

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