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1-(4-Nitrophenyl)piperazine → HCID 18403833, 화합물

HRID 1017685
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HRID 1017685 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([NH:14][CH3:15])=[O:13])[CH:6]=O.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1)([O-:18])=[O:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][N:28]2[CH2:29][CH2:30][N:25]([C:22]3[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:24][CH:23]=3)[CH2:26][CH2:27]2)[CH:8]=[CH:9][C:10]=1[O:11][C:12]([NH:14][CH3:15])=[O:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 804471-(4-Nitrophenyl)piperazineHCID 4064704HCID 4064704, 화합물HCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 18403833HCID 18403833, 화합물수율 86%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of 3-methoxy-4-(methylaminocarbonyloxy)benzaldehyde (1.01 g) in 1,2-dichloroethane (19.0 ml) was added 1-(4-nitrophenyl)piperazine (1.0 g), and sodium triacetoxyborohydride (1.54 g), with stirring. The reaction mixture was stirred for 3 hrs at ambient temperature, poured into ice/saturated sodium carbonate solution (100 ml) and extracted with dichloromethane. The combined organic extracts were washed with water and brine, dried over sodium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed (silica gel), eluting with dichloromethane, followed by 1% methanol:dichloromethane. The appropriate fractions were collected and concentrated to give 1.66 g (86%) of product. Recrystallization from ethyl acetate gave the analytical sample, mp 155-157° C.

후처리

  1. stirringThe reaction mixture was stirred for 3 hrs at ambient temperature
  2. extractionextracted with dichloromethane
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customchromatographed (silica gel)
  8. washeluting with dichloromethane
  9. customThe appropriate fractions were collected
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-426a0a58db0645b7aeb460946f838425
출처 데이터셋
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06479495B1

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