Formamide → HCID 13364160, compound

HRID 617000Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[CH2:13][CH2:12][CH:11]([N:14]3[CH2:19][CH2:18][C:17]([C:27](=[O:29])[NH2:28])([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:37](N)=O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)[CH2:9][CH2:10][CH:11]([N:14]3[CH2:19][CH2:18][C:17]4([N:20]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH2:37][NH:28][C:27]4=[O:29])[CH2:16][CH2:15]3)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 170 °C

Procedure

To 16 g of 1-[4,4-bis(p-fluorophenyl)cyclohexyl]-4-carbamoyl-4-anilinopiperidine is added 30 g of formamide, the temperature is raised slowly, and the mixture is heated at 170° C for 14 hours. After cooling water is added to the reaction mixture, and the aqueous mixture is extracted with chloroform. The extract is washed with water and dried over sodium sulfate, and the solvent is removed. The precipitated crystals are collected by filtration and recrystallized from chloroform to give 8-[4,4-bis(p-fluorophenyl)cyclohexyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one as white crystals, melting at 249°-253° C.

Workup

temperaturethe temperature is raised slowly
additionis added to the reaction mixture
extractionthe aqueous mixture is extracted with chloroform
washThe extract is washed with water
dry with materialdried over sodium sulfate
customthe solvent is removed
filtrationThe precipitated crystals are collected by filtration
customrecrystallized from chloroform

Sources & evidence

ORD record: ord-da338671bc914d5f864db3309d7178db
Source dataset: uspto-grants-1978_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04076821

Reaction notes

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