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Hydrochloric Acid → 4-(4-Methylpiperazin-1-yl)-3-[(4-methylpiperazin-1-yl)methyl]aniline

HRID 1190865
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HRID 1190865 반응식
Cl[Sn]Cl.Cl.[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=2[CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)[CH2:8][CH2:7]1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH3:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[CH2:21][N:22]2[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]2)[CH2:10][CH2:11]1
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 672468861-Methyl-4-{2-[(4-methylpiperazin-1-yl)methyl]-4-nitrophenyl}piperazine

생성물 1

HCID 672492344-(4-Methylpiperazin-1-yl)-3-[(4-methylpiperazin-1-yl)methyl]aniline수율 63%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

A mixture of SnCl2 (0.398 g, 2.1 mmol), 1.6 mL of HCl 1M and 5 mL of THF was added to a solution of 1-methyl-4-{2-[(4-methylpiperazin-1-yl)methyl]-4-nitrophenyl}piperazine (0.175 g, 2.5 eq) in 15 mL of THF. The reaction mixture was refluxed for 3 h and allowed to cool to room temperature. A saturated aqueous solution of Na2CO3 was added. The aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (DCM/MeOH/NH4OH//8/2/0.1) to yield expected compound as a brown oil (100 mg, 63% yield).

후처리

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (DCM/MeOH/NH4OH//8/2/0.1)

출처 및 근거

ORD 기록
ord-6040fbecdcbf43869eac1b2d1a3fe700
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08680095B2

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