Formaldehyde → 4-Methyl-3-(4-nitrophenyl)piperazine-2-one

HRID 1772090노트

반응식

HRID 1772090 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11](=[O:16])[NH:12][CH2:13][CH2:14][N:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C=O.O.[C:20]([BH3-])#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:20][N:15]1[CH2:14][CH2:13][NH:12][C:11](=[O:16])[CH:10]1[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

참가 물질

8

반응물 5

HCID 712FormaldehydeHCID 962WaterHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 57625103HCID 57625103, 화합물

생성물 1

HCID 666098864-Methyl-3-(4-nitrophenyl)piperazine-2-one수율 100%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 887Methanol용매2회

실험 절차

A 10-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen, charged with 104a (196 mg, 0.89 mmol), 37% solution of formaldehyde in water (35 mg, 1.16 mmol) and anhydrous methanol (3 mL). A solution of sodium cyanoborohydride (169 mg, 2.68 mmol) and anhydrous zinc chloride (183 mg, 1.34 mmol) in anhydrous methanol (3 mL) was added, and the reaction was stirred at room temperature for 1 h. After this time, 1N aqueous sodium hydroxide (2 mL) was added, and the methanol was evaporated under reduced pressure. The remaining aqueous solution was extracted with ethyl acetate (3×25 mL). The organic layers were combined, washed with water (20 mL) and brine (20 mL) and dried over magnesium sulfate. The drying agent was removed by filtration and the filtrate concentrated under reduced pressure to afford 104b in 100% yield (210 mg) as a yellow solid: mp 185-186° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.18 (d, 2H, J=8.1 Hz), 8.05 (d, 1H, J=3.6 Hz), 7.63 (d, 2H, J=7.8 Hz), 3.82 (s, 1H), 3.45 (m, 1H), 3.17 (m, 1H), 2.95 (m, 1H), 2.56 (m, 1H), 2.06 (s, 3H); MS (ESI+) m/z 236 (M+H).

후처리

  1. customA 10-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. customthe methanol was evaporated under reduced pressure
  4. extractionThe remaining aqueous solution was extracted with ethyl acetate (3×25 mL)
  5. washwashed with water (20 mL) and brine (20 mL)
  6. dry with materialdried over magnesium sulfate
  7. customThe drying agent was removed by filtration
  8. concentrationthe filtrate concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-deefc191e6d5456da08f9a77fd254cde
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249123B2

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