N,N-Diethylpiperazine-1-carboxamide → HCID 13690989, compound

HRID 2290782Notes

Reaction equation

Cl[CH2:2][C:3]1[N:7]=[C:6]([CH:8]([CH3:22])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[O:5][N:4]=1.[CH2:23]([N:25]([CH2:34][CH3:35])[C:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)=[O:27])[CH3:24]>CN(C=O)C>[CH2:34]([N:25]([CH2:23][CH3:24])[C:26]([N:28]1[CH2:29][CH2:30][N:31]([CH2:2][C:3]2[N:7]=[C:6]([CH:8]([CH3:22])[C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:11]([F:21])[CH:10]=3)[O:5][N:4]=2)[CH2:32][CH2:33]1)=[O:27])[CH3:35]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2.14 g of 3-chloromethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole, 2.54 g of N,N-diethyl-1-piperazine carboxamide and 15 ml of dry DMF was heated at 100° C. for 2 hours. After cooling, the reaction mixture was poured into ice-water and extracted with diethyl ether. The organic phase was washed with water, dried over magnesium sulfate and evaporated. The residue was chromatographed over silica gel using chloroform-methanol (50:1, v/v) to yield 2.43 g of 3-[4-(N,N-diethylcarbamoyl)piperazinomethyl]-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole as a light brown oil. To a solution of this product in ethanol was added equal mole of ethanolic hydrogen chloride and the mixture was concentrated to dryness under reduced pressure. Recrystallization of the residue from ethanol-diethyl ether gave colorless crystals, m.p. 181°-182° C.

Workup

temperatureAfter cooling
extractionextracted with diethyl ether
washThe organic phase was washed with water
dry with materialdried over magnesium sulfate
customevaporated
customThe residue was chromatographed over silica gel

Sources & evidence

ORD record: ord-94a6bd1a287e4b93b036c74d0620cede
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04618617

Reaction notes

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