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

HRID 1633880ノート

反応式

HRID 1633880 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-79184d3f718c4a2398fdadd987c32f79
出典データセット
uspto-grants-2003_01
特許番号
US06504031B1

反応ノート

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