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Sodium Hydroxide → 5,6,10,11-Tetrahydro-2-methoxy-8-methylbenzo[g]pyrazino[1,2-a]indole fumarate

HRID 486591
ノート
印刷プレビュー

反応式

HRID 486591 の反応式
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]2[CH2:7][CH2:8][C:9]3[CH:10]=[CH:11][N:12]([CH2:14][CH2:15][NH:16][C:17](=O)[CH3:18])[C:13]=3[C:5]=2[CH:4]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33]>C(O)C>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33].[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]2[CH2:7][CH2:8][C:9]3[CH:10]=[C:11]4[C:17]([CH3:18])=[N:16][CH2:15][CH2:14][N:12]4[C:13]=3[C:5]=2[CH:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 19036540N-[2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)ethyl]-acetamide

生成物 1

HCID 190953875,6,10,11-Tetrahydro-2-methoxy-8-methylbenzo[g]pyrazino[1,2-a]indole fumarate収率 84%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

反応条件

温度
50 °C

実験手順

N-[2-(4,5-Dihydro-8-methoxy-1H-benzo[g]indol-1-yl)-ethyl]acetamide (4.7 g) was treated with 15 ml of phosphorus oxychloride under argon and the mixture was stirred at 50° C. for 30 minutes. The cooled mixture was added to 2000 g of ice-water and treated with 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. 4.2 g of residue were chromatographed on 250 g of aluminium oxide (neutral, III) with methylene chloride as the eluent. 3.8 g of crude product 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 4.7 g (84%) of 5,6,10,11-tetrahydro-2-methoxy-8-methylbenzo[g]pyrazino[1,2-a]indole fumarate (1:1); m.pt.: 175°-177° 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. custom4.2 g of residue were chromatographed on 250 g of aluminium oxide (neutral, III) with methylene chloride as the eluent
  4. dissolution3.8 g of crude product were dissolved in a 20-fold amount of hot ethanol

出典と根拠

ORDレコード
ord-d7d5b841e9874ecd910cd517555c36b5
出典データセット
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05292732

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート