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Hydrochloric Acid → 5-(2-Piperazin-1-ylethyl)-2,1,3-benzoxadiazole

HRID 1519503
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HRID 1519503 반응식
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[CH:7]=[CH:6][C:5]=12.Cl>O1CCOCC1>[N:12]1([CH2:11][CH2:10][C:8]2[CH:7]=[CH:6][C:5]3=[N:1][O:2][N:3]=[C:4]3[CH:9]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1
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참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 66646566Tert-butyl 4-[2-(2,1,3-benzoxadiazol-5-yl)ethyl]piperazine-1-carboxylate

생성물 1

HCID 151663825-(2-Piperazin-1-ylethyl)-2,1,3-benzoxadiazole

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

tert-Butyl 4-[2-(2,1,3-benzoxadiazol-5-yl)ethyl]piperazine-1-carboxylate (470 mg, 1.4 mmol) was then dissolved in dioxane (10 mL) and added 7 mL of 4M HCl in dioxane. The reaction was stirred at room temperature overnight. Evaporated off all solvent and the residue was taken up in ethyl acetate basified with 1N NaOH. The ethyl acetate was separated and washed with brine then dried over Na2SO4 and evaporated to dryness. The residue was purified by chromatography using 5% (NH4OH:MeOH 1:10) in 95% DCM to yield 5-(2-piperazin-1-ylethyl)-2,1,3-benzoxadiazole. 1H-NMR (600 MHz, CDCl3): δ 7.72 (d, J=9.2 Hz, 1H), 7.28 (d, J=9.2 Hz, 1H), 2.92 (t, J=4.9 Hz, 2H), 2.88 (t, J=7.6 Hz, 1H), 2.65 (t, J=7.6 Hz, 1H). LC-MS: M+1=233.

후처리

  1. customEvaporated off all solvent
  2. customThe ethyl acetate was separated
  3. washwashed with brine
  4. dry with materialthen dried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-02749bc007e74dbea5088a57667fe333
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073882B2

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