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Sodium Bicarbonate → tert-Butyl 4-((4-aminophenyl)methyl)piperazine-1-carboxylate

HRID 499198
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HRID 499198 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O.[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 235069461-Boc-4-(4-Nitrobenzyl)piperazineHCID 85782573Tin tetrachloride dihydrate

생성물 1

HCID 12045001tert-Butyl 4-((4-aminophenyl)methyl)piperazine-1-carboxylate수율 89%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

4-(4-Nitro-benzyl)-piperazin-1-yl carboxylic acid tert-butyl ester (769 mg, 2.4 mmol) and tin chloride dihydrate (2.70 g, 12 mmol) are suspended in ethyl acetate (20 mL) and stirred at room temperature overnight. Then, saturated aqueous solution of sodium bicarbonate (20 mL) is added and vigorously stirred for 1 hour. Solids are removed by filtration and the organic layer of the filtrate is separated and washed with water (20 mL). The organic phase is dried over anhydrous magnesium sulfate and concentrated to give a white solid (620 mg, 89% yield, ES+(m/z) 293 [M+H]).

후처리

  1. stirringvigorously stirred for 1 hour
  2. customSolids are removed by filtration
  3. customthe organic layer of the filtrate is separated
  4. washwashed with water (20 mL)
  5. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give a white solid (620 mg, 89% yield, ES+(m/z) 293 [M+H])

출처 및 근거

ORD 기록
ord-22a6201100424ded8c68ca25f011162c
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07767674B2

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