Methanol → HCID 9841354, 화합물

HRID 1057648노트

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HRID 1057648 반응식
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([Cl:21])=[C:16]([O:22][CH2:23][C:24]#[N:25])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>C1COCC1>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([Cl:21])=[C:16]([O:22][CH2:23][CH2:24][NH2:25])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 887MethanolHCID 18671666HCID 18671666, 화합물

생성물 1

HCID 9841354HCID 9841354, 화합물수율 70%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

To [(9-benzyl-3-chloro-9H-carbazol-4-yl)oxy]acetonitrile (0.292 g, 0.842 mmol) in THF (6 mL) is added borane-methyl sulfide complex (0.24 mL, 2.53 mmol). The mixture is stirred at 80° C. for 2.5 h and then allowed to cool. MeOH is carefully added to the residue until gas evolution ceased and then the mixture is concentrated under vacuum. MeOH addition/removal is repeated two more times and then MeOH-dichloromethane (about 2 mL each) is added, followed by several drops of conc. HCl. The mixture is stirred for about 15 min and then taken to dryness under vacuum. After partitioning with dichloromethane and aq. sodium bicarbonate and drying, the residue is chromatographed on silica gel (50 mL) using MeOH-dichloromethane (2/98 to 4/96) to give 0.206 g (70%) of 2-[(9-benzyl-3-chloro-9H-carbazol-4-yl)oxy]ethylamine. The methanesulfonate salt is prepared by dissolving 2-[(9-benzyl-3-chloro-9H-carbazol-4-yl)oxy]ethylamine in MeOH and dichloromethane and adding methanesulfonic acid (0.0581 g). The mixture is concentrated to dryness under vacuum and the residue is crystallized from dichloromethane-hexane to give 0.206 g of 2-[(9-benzyl-3-chloro-9H-carbazol-4-yl)oxy]ethylamine, methanesulfonate salt as a white crystalline solid. 1H NMR (CDCl3) δ1.9, 3.29, 4.31, 5.49, 7.07, 7.12, 7.27, 7.35-7.49, 8.32.

후처리

  1. temperatureto cool
  2. concentrationthe mixture is concentrated under vacuum
  3. customMeOH addition/removal
  4. additionMeOH-dichloromethane (about 2 mL each) is added
  5. stirringThe mixture is stirred for about 15 min
  6. customAfter partitioning with dichloromethane and aq. sodium bicarbonate
  7. customdrying
  8. customthe residue is chromatographed on silica gel (50 mL)

출처 및 근거

ORD 기록
ord-55517286cefe4e3da610e3b6166d9f36
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514968B1

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