Water → HCID 14349113、化合物

HRID 414825

反応式

HRID 414825 の反応式
[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

参加物

6

反応物 5

HCID 962WaterHCID 6228Dimethylformamide2 回HCID 24758Sodium hydrideHCID 740281,2-Dichloro-4-fluorobenzeneHCID 13118512HCID 13118512、化合物

生成物 1

HCID 14349113HCID 14349113、化合物収率 57%

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ec49c880435b4f18b7729301aa2b6e48
出典データセット
uspto-grants-1988_12
特許番号
US04794181

関連ノート

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