Sodium Chloride → 2-(6-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)-ethylamine fumarate

HRID 264549ノート

反応式

HRID 264549 の反応式
[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][N:13]([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[C:14]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-:21].[K+].[Cl-].[Na+].[CH2:25]([OH:28])[CH2:26]O.[OH2:29]>>[C:18]([OH:20])(=[O:29])/[CH:19]=[CH:26]/[C:25]([OH:28])=[O:21].[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][N:13]([CH2:15][CH2:16][NH2:17])[C:14]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 19036432HCID 19036432、化合物HCID 20437942Ethylene glycol water

生成物 1

HCID 190364442-(6-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)-ethylamine fumarate収率 62%

実験手順

1.80 g of N-[6-chloro-2-(4,5-dihydro-1H-benz[g]indol-1-yl)ethyl]-acetamide were heated to 140° for 20 hours under argon in 17 ml of ethylene glycol/water 12:5 in the presence of 0.9 g of potassium hydroxide. The mixture was left to cool and was treated with 140 ml of semi-saturated sodium chloride solution. The mixture was extracted three times with diethyl ether. The combined extracts were washed once with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. The brown oil was chromatographed on 50 g of silica gel with dichloromethane/methanol (19:1, then 9:1). The crude product was dissolved in 7 ml of diethyl ether and 0.98 g of fumaric acid was added. The solvent was removed in a vacuum and the residue was recrystallized from 50 ml of chloroform/ethanol 4:1. 1.41 g (62%) of 2-(6-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)-ethylamine fumarate (1:1) with m.p. 187°-188° were obtained.

後処理

  1. waitThe mixture was left
  2. temperatureto cool
  3. extractionThe mixture was extracted three times with diethyl ether
  4. washThe combined extracts were washed once with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe brown oil was chromatographed on 50 g of silica gel with dichloromethane/methanol (19:1
  9. dissolutionThe crude product was dissolved in 7 ml of diethyl ether
  10. addition0.98 g of fumaric acid was added
  11. customThe solvent was removed in a vacuum
  12. customthe residue was recrystallized from 50 ml of chloroform/ethanol 4:1

出典と根拠

ORDレコード
ord-015fd6120e6c45909c905e8e4c9d14a3
出典データセット
uspto-grants-1997_07
特許番号
US05646173

反応ノート

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