Ethanol → 4-Ethyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1633880노트

반응식

HRID 1633880 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([CH2:12][CH3:13])[CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.C=O.[OH-].[K+].[CH2:18](O)C>C(O)=O>[CH2:12]([CH:9]1[C:5]2[C:6](=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:18][NH:11][CH2:10]1)[CH3:13]

참가 물질

6

반응물 4

HCID 702EthanolHCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 145280732-(3-Methoxyphenyl)butan-1-amine

생성물 1

HCID 186800734-Ethyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

A solution of 2-(3-methoxyphenyl)-1-butanamine (25 g, 131 mmol, prepared according to the procedure described in J. Med. Chem. 1990, 33, 153-160) in formic acid (120 mL) at room temperature was treated with paraformaldehyde (4.18 g, 131 mmol), stirred for 16 hours, treated with 25% KOH (30 mL) and ethanol (100 mL), and refluxed for 2.5 hours. The mixture was cooled to room temperature, extracted with dichloromethane, and the combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with dichloromethane to provide the desired product.

후처리

  1. temperaturerefluxed for 2.5 hours
  2. extractionextracted with dichloromethane
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with dichloromethane

출처 및 근거

ORD 기록
ord-79184d3f718c4a2398fdadd987c32f79
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06504031B1

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