Water → HCID 14349113, 화합물

HRID 414825

반응식

HRID 414825 반응식
[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[CH:7]([OH:12])[CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.[H-].[Na+].[Cl:19][C:20]1[CH:21]=[C:22](F)[CH:23]=[CH:24][C:25]=1[Cl:26].[OH2:28].CN(C)C=[O:32]>>[C:14]([OH:15])(=[O:32])[C:3]([OH:2])=[O:28].[Cl:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][C:25]=1[Cl:26])[O:12][CH:7]1[C:6]2[CH:13]=[C:14]([O:15][CH3:16])[C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:11][CH2:10][NH:9][CH2:8]1

참가 물질

6

반응물 5

HCID 962WaterHCID 6228Dimethylformamide2회HCID 24758Sodium hydrideHCID 740281,2-Dichloro-4-fluorobenzeneHCID 13118512HCID 13118512, 화합물

생성물 1

HCID 14349113HCID 14349113, 화합물수율 57%

반응 조건

온도
60 °C

실험 절차

A solution of 7,8-dimethoxy-1-hydroxy-2,3,4,5-tetrahydro-3-benzazepine (3 g, 13.4 mmole) in 25 ml dimethylformamide was slowly dropped into a stirring suspension of sodium hydride (50% oil dispersion, 0.7 g, 14.8 mmole), previously washed with hexane, in 10 ml dimethylformamide. After the addition was completed, the mixture was warmed for one hour at 60° C., then was cooled and a solution of 3,4-dichlorofluorobenzene (2.4 g, 14.8 mmole) in 10 ml dimethylformamide was added. After stirring two hours at ambient temperature, the reaction mixture was stirred with 400 ml water and was extracted with ethyl acetate. The organic extract was washed with ethyl acetate. The organic extract was washed with water and saturated NaCl and was dried (anhydrous MgSO4), filtered and evaporated to 7 g of an oil. This oil was purified by HPLC (silica gel, 5% methanol in dichloromethane) to give 2.8 g (57%) of an oil. This oil was converted to the oxalate salt as in Example 1 and was recrystallized from ethyl acetate-methanol to give 2.1 g (34%) of 1,(3-4-dichlorophenoxy)-7,8-dimethoxy-2,3,4,5-tetrahydro-3-benzazepine oxalate, d 167°-168° C.

후처리

  1. washpreviously washed with hexane, in 10 ml dimethylformamide
  2. additionAfter the addition
  3. temperaturewas cooled
  4. extractionwas extracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with ethyl acetate
  7. extractionThe organic extract
  8. washwas washed with water and saturated NaCl
  9. dry with materialwas dried (anhydrous MgSO4)
  10. filtrationfiltered
  11. customevaporated to 7 g of an oil
  12. customThis oil was purified by HPLC (silica gel, 5% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-ec49c880435b4f18b7729301aa2b6e48
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04794181

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