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

HRID 1772090ノート

反応式

HRID 1772090 の反応式
[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

参加物

8

反応物 5

HCID 712FormaldehydeHCID 962WaterHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 57625103HCID 57625103、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-deefc191e6d5456da08f9a77fd254cde
出典データセット
uspto-grants-2016_02
特許番号
US09249123B2

反応ノート

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