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

HRID 38310

반응식

HRID 38310 반응식
[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

참가 물질

5

반응물 3

HCID 4101HexamethylenetetramineHCID 8421HomoveratrylamineHCID 23437676Trifluoroacetic acid acetate

생성물 1

HCID 300583,4-Dihydro-6,7-dimethoxyisoquinoline수율 95%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-ee60041f966b45bd8141886f41499c14
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524733B2

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