Hydrochloric Acid → 3-(4-Aminophenyl)-4-ethylpiperazin-2-one

HRID 1363509노트

반응식

HRID 1363509 반응식
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][C:5](=[O:9])[CH:4]1[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)[CH3:2].Cl.C(=O)([O-])[O-].[K+].[K+]>[Fe].C(O)C>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH:4]2[N:3]([CH2:1][CH3:2])[CH2:8][CH2:7][NH:6][C:5]2=[O:9])=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 57625097HCID 57625097, 화합물

생성물 1

HCID 576251673-(4-Aminophenyl)-4-ethylpiperazin-2-one수율 100%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

A 25-mL single-neck round-bottomed flask equipped with a reflux condenser and magnetic stirrer was purged with nitrogen and charged with 32 (210 mg, 0.89 mmol), ethanol (6 mL), iron powder (−325 mesh, 491 mg, 8.93 mmol) and 2N hydrochloric acid (0.70 mL, 1.40 mmol), and the mixture was heated at reflux for 30 min. After this time, the reaction was cooled to room temperature, and powdered potassium carbonate (3.03 g, 22.0 mmol) was added. The resulting suspension was filtered and the filter cake washed with ethanol (4×10 mL). The filtrate was concentrated under reduced pressure to afford 33 in 100% yield (185 mg) as a white solid: mp 153-154° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.74 (d, 1H, J=2.7 Hz), 6.90 (d, 2H, J=8.4 Hz), 6.47 (d, 2H, J=8.4 Hz), 4.95 (bs, 2H), 3.45 (m, 1H), 3.42 (s, 1H), 3.14 (m, 1H), 2.89 (m, 1H), 2.44 (m, 1H), 2.02 (s, 3H); MS (ESI+) m/z 206 (M+H).

후처리

  1. customA 25-mL single-neck round-bottomed flask equipped with a reflux condenser and magnetic stirrer
  2. customwas purged with nitrogen
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 30 min
  5. filtrationThe resulting suspension was filtered
  6. washthe filter cake washed with ethanol (4×10 mL)
  7. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8b4906595d334a318388048caf217b28
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884108B2

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