Sodium Hydroxide → 4-Chloro-5,6,10,11-tetrahydro-8-methylbenz[g]pyrazino[1,2-a]indole fumarate

HRID 486538ノート

反応式

HRID 486538 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)[CH3:19])[C:14]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>C(O)C>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][C:10]3[CH:11]=[C:12]4[C:18]([CH3:19])=[N:17][CH2:16][CH2:15][N:13]4[C:14]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 14798Sodium Hydroxide2 回HCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 19036432HCID 19036432、化合物

生成物 1

HCID 190953764-Chloro-5,6,10,11-tetrahydro-8-methylbenz[g]pyrazino[1,2-a]indole fumarate収率 82%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

N-[2-(6-Chloro-4,5-dihydro-1H-benz[g]indol-1-yl)ethyl]acetamide (6.0 g) was treated with 30 ml of phosphorus oxychloride and the mixture was stirred at 100° C. for 30 minutes. The cooled mixture was added to 2500 g of ice-water and treated with 100 ml of 2N sodium hydroxide solution and 200 ml of 28% sodium hydroxide solution. The mixture was extracted once with 300 ml of methylene chloride and twice with 100 ml of methylene chloride each time, the organic phases were combined, dried with MgSO4 and freed from solvent. 5.7 g of residue were dissolved in a 20-fold amount of hot ethanol and treated while hot with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There were obtained 6.6 g (82%) of 4-chloro-5,6,10,11-tetrahydro-8-methylbenz[g]pyrazino[1,2-a]indole fumarate (1:1); m.pt.: 191°-192° C. (dec.).

後処理

  1. extractionThe mixture was extracted once with 300 ml of methylene chloride and twice with 100 ml of methylene chloride each time
  2. dry with materialdried with MgSO4
  3. dissolution5.7 g of residue were dissolved in a 20-fold amount of hot ethanol

出典と根拠

ORDレコード
ord-986ca584e5c946aaa05920797662f876
出典データセット
uspto-grants-1994_03
特許番号
US05292732

反応ノート

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