Hexamethylenetetramine → 3,4-Dihydro-6,7-dimethoxyisoquinoline

HRID 38310

反応式

HRID 38310 の反応式
[C:1](O)(=O)C.FC(F)(F)C(O)=O.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH2:22][CH2:23][NH2:24])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].C1N2CN3CN(C2)CN1C3>O>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[CH:1]=[N:24][CH2:23][CH2:22]2

参加物

5

反応物 3

HCID 4101HexamethylenetetramineHCID 8421HomoveratrylamineHCID 23437676Trifluoroacetic acid acetate

生成物 1

HCID 300583,4-Dihydro-6,7-dimethoxyisoquinoline収率 95%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Acetic acid/trifluoroacetic acid (100 mL) was added to a solution of 2-(3,4-dimethoxyphenyl)ethanamine (20 g, 110.38 mmol, 1.00 equiv) and hexamethylenetetramine (31 g, 221.11 mmol, 2.00 equiv). The resulting solution was heated at reflux for about 5 hours in an oil bath. After adding water (100 mL), the solution was extracted with dichloromethane (3×200 mL), and the organic layers were combined and dried over anhydrous sodium sulfate. Solids were removed by filtration, and the resulting filtrate was concentrated in vacuo to give the title product as a yellow oil (20 g, yield=95%). LC-MS: m/z=192 (MH)+.

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for about 5 hours in an oil bath
  3. extractionthe solution was extracted with dichloromethane (3×200 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customSolids were removed by filtration
  6. concentrationthe resulting filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-ee60041f966b45bd8141886f41499c14
出典データセット
uspto-grants-2013_09
特許番号
US08524733B2

関連ノート

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