Methanol → N-ethyl-2-[(5-methyl-1-phenyl-1,2-dihydro [1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]-1-ethanamine

HRID 1279712노트

반응식

HRID 1279712 반응식
[CH3:1][C:2]1[CH:3]=[C:4]2[C:12]3=[C:13]([O:15][CH2:16][CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:11]3[C:10]3[CH:9]=[CH:8][CH:7]=[C:6]([O:24][CH2:25][CH2:26][NH:27][C:28](=O)[CH3:29])[C:5]2=3)[CH:14]=1.CO>C1COCC1>[CH2:28]([NH:27][CH2:26][CH2:25][O:24][C:6]1[C:5]2[C:4]3[C:12]4=[C:13]([O:15][CH2:16][CH:17]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[N:11]4[C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH:14]=[C:2]([CH3:1])[CH:3]=3)[CH3:29]

참가 물질

4

반응물 2

HCID 887MethanolHCID 12148635N-{2-[(5-methyl-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]ethyl}acetamide

생성물 1

HCID 9821559N-ethyl-2-[(5-methyl-1-phenyl-1,2-dihydro [1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]-1-ethanamine수율 72.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
85 °C

실험 절차

To a mixture of N-{2-[(5-methyl-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]ethyl}acetamide (0.212 g, 0.53 mmol) in THF (10 mL) is added borane-methylsulfide complex (0.15 mL, 1.6 mmol). The mixture is refluxed at 85° C. for 16 hours. After cooling, methanol is slowly added until gas evolution ceased. The solvents are removed under vacuum and methanol (5 mL) is added then removed. The residue is dissolved in CH2C2/CH3OH (1:5, 15 mL). Conc. HCl is added and the mixture is heated at 65° C. for 1 h. The mixture is removed from heat, neutralized with aqueous potassium carbonate and then partitioned between water and CH2Cl2. The organic layer is washed with water, dried over magnesium sulfate, and concentrated. Column chromatography (70 g silica gel) using CH3OH/CH2C2 (5:95) as eluent gave 0.148 g (70%) of N-ethyl-2-[(5-methyl-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]-1-ethanamine (TLC: MeOH/CH2C2, 5/95, Rf=0.38); conversion to the maleic acid salt and recrystallizing from absolute ethanol gave 0.0223 g of N-ethyl-2-[(5-methyl-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]-1-ethanamine, maleic acid salt.

후처리

  1. additionis added borane-methylsulfide complex (0.15 mL, 1.6 mmol)
  2. temperatureAfter cooling
  3. customThe solvents are removed under vacuum and methanol (5 mL)
  4. additionis added
  5. customthen removed
  6. dissolutionThe residue is dissolved in CH2C2/CH3OH (1:5, 15 mL)
  7. additionConc. HCl is added
  8. temperaturethe mixture is heated at 65° C. for 1 h
  9. customThe mixture is removed
  10. temperaturefrom heat
  11. custompartitioned between water and CH2Cl2
  12. washThe organic layer is washed with water
  13. dry with materialdried over magnesium sulfate
  14. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3bfa5431c9244aeda5e58de7dc05a79e
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448397B1

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