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

HRID 2290782노트

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HRID 2290782 반응식
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]

참가 물질

4

반응물 2

HCID 67067N,N-Diethylpiperazine-1-carboxamideHCID 136909413-Chloromethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

생성물 1

HCID 13690989HCID 13690989, 화합물수율 77.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

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.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed over silica gel

출처 및 근거

ORD 기록
ord-94a6bd1a287e4b93b036c74d0620cede
출처 데이터셋
uspto-grants-1986_10
특허 번호
US04618617

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