Water → 2,6-Bis(2-methylphenyl)-1-methyl-4-piperidone

HRID 77690노트

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HRID 77690 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10](=[O:20])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].[CH3:21][NH2:22].O>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:9][C:10](=[O:20])[CH2:11][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[N:22]1[CH3:21]

참가 물질

5

반응물 3

HCID 962WaterHCID 6329MethylamineHCID 45639421,5-Bis(2-methylphenyl)-1,4-pentadien-3-one

생성물 1

HCID 695017532,6-Bis(2-methylphenyl)-1-methyl-4-piperidone수율 52%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1,5-Bis(2-methylphenyl)-1,4-pentadien-3-one (20ac, 0.50 g, 1.9 mmol) was dissolved in dimethyl formamide (10 ml). Methylamine (51, 1.0 ml, 11.6 mmol, 40% in water) was added and the mixture stirred for 24 hr at room temperature. The mixture was poured into water (50 ml) and stirred for 2 hr at room temperature. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was chromatographed on silica gel with ethyl acetate/hexane to afford a solid that was recrystallized from ethanol to give 0.29 g (52%) of a white solid: mp 155-157° C.; 1H NMR δ 1.82, (s, 3H), 2.40, (s, 6H), 2.44 (d, 2H, J=11.9 Hz), 2.77 (t, 2H, J=13.3 Hz), 3.74 (d, 2H, J=11.9 Hz), 7.16 (m, 6H), 7.67, (d, 2H, J=7.0 Hz); 13C NMR: δ 19.5, 39.9, 49.3, 65.8, 126.7, 126.9, 130.6, 134.8, 140.9, 207.2; Exact mass calcd for C20H23NO: 293.1779, observed (M+H) 294.1856.

후처리

  1. stirringstirred for 2 hr at room temperature
  2. extractionThe resulting mixture was extracted into ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was chromatographed on silica gel with ethyl acetate/hexane
  9. customto afford a solid
  10. customthat was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-722b94e03ebc41f8bea43567a9cf4e60
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841326B2

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