Morpholine → (1H-Indol-6-yl)(morpholino)methanone

HRID 1685558노트

반응식

HRID 1685558 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=2)[CH:3]=[CH:2]1.[C:13](C1NC=CN=1)([C:15]1N[CH:17]=[CH:18][N:19]=1)=[O:14].N1CCOCC1>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([N:19]3[CH2:15][CH2:13][O:14][CH2:17][CH2:18]3)=[O:12])[CH:8]=2)[CH:3]=[CH:2]1

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 5952301H-indole-6-carboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

생성물 1

HCID 39710543(1H-Indol-6-yl)(morpholino)methanone수율 86.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Indole-6-carboxylic acid (0.60 g, 3.7 mmol) was dissolved in DCM (15 mL) and carbonyl diimidazole (0.63 g, 3.9 mmol) was added and the reaction mixture was refluxed under N2 for 30 min. The mixture was allowed to cool to room temperature before morpholine (0.39 g, 4.5 mmol) was added and the reaction mixture was refluxed for 16 hours. The mixture was allowed to cool to room temperature before it was washed in sequence with HCl (50 mL, 1 N in water), NaOH (50 mL, 1 N in water) and brine (50 mL). The organic phase was dried with MgSO4, and the solvent was removed in vacuo to give 0.74 g of (1H-indol-6-yl)-morpholin-4-yl-methanone.

후처리

  1. temperaturethe reaction mixture was refluxed under N2 for 30 min
  2. additionwas added
  3. temperaturethe reaction mixture was refluxed for 16 hours
  4. washwas washed in sequence with HCl (50 mL, 1 N in water), NaOH (50 mL, 1 N in water) and brine (50 mL)
  5. dry with materialThe organic phase was dried with MgSO4
  6. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-968c67c9de044af7b33e23badd508a5c
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148413B2

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