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 1279712ノート

反応式

HRID 1279712 の反応式
[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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3bfa5431c9244aeda5e58de7dc05a79e
出典データセット
uspto-grants-2002_09
特許番号
US06448397B1

反応ノート

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