Benzofuran-2-carboxylic acid → Piperazine, 1-(2-benzofuranylcarbonyl)-4-((3,4,5-trimethoxyphenyl)methyl)-, monohydrochloride

HRID 2108097노트

반응식

HRID 2108097 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([OH:12])=O.[ClH:13].Cl.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[CH2:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(P(=O)(OCC)OCC)#N.C(OCC)(=O)C.Cl>CCCCCC.C(OCC)(=O)C.O.CN(C)C=O.C(N(CC)CC)C>[ClH:13].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([N:24]1[CH2:23][CH2:22][N:21]([CH2:20][C:19]2[CH:27]=[C:28]([O:32][CH3:33])[C:29]([O:30][CH3:31])=[C:17]([O:16][CH3:15])[CH:18]=2)[CH2:26][CH2:25]1)=[O:12]

참가 물질

10

반응물 4

HCID 10331Benzofuran-2-carboxylic acidHCID 76257Diethyl cyanophosphonateHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochlorideHCID 21866389Hydrogen chloride-ethyl acetate

생성물 1

HCID 3038617Piperazine, 1-(2-benzofuranylcarbonyl)-4-((3,4,5-trimethoxyphenyl)methyl)-, monohydrochloride수율 47.2%

시약·촉매·용매 5

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8058Hexane용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 2-benzofuranecarboxylic acid (0.5 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (1.1 g), triethylamine (1.2 g) and N,N-dimethylformamide (20 ml) is added dropwise, while stirring at room temperature, diethyl cyanophosphonate (1.2 ml), followed by stirring for one hour at room temperature. After addition of water (100 ml), ethyl acetate (100 ml) and hexane (100 ml), the mixture is extracted with ethyl acetate. The organic layer is washed with water, dried, and concentrated under reduced pressure. The residue is purified by means of a silica gel column chromatography (hexane:ethyl acetate:acetone=1:1:0.5) to give an oily product, to which is added 1N hydrogen chloride - ethyl acetate solution (10 ml) to cause precipitation of powder. The powdery product is collected by filtration and recrystallized from a mixture of methanol - ethyl acetate to give 1-(2-benzofuranylcarbonyl)4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (0.65 g) as colorless needles, m.p. 221°-225° C. (decomp.).

후처리

  1. additionis added dropwise
  2. stirringby stirring for one hour at room temperature
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by means of a silica gel column chromatography (hexane:ethyl acetate:acetone=1:1:0.5)
  8. customto give an oily product
  9. customprecipitation of powder
  10. filtrationThe powdery product is collected by filtration
  11. customrecrystallized from a mixture of methanol - ethyl acetate

출처 및 근거

ORD 기록
ord-c9010a967ad149b091f9d325d01e6853
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04937246

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