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

HRID 1633880Notes

Reaction equation

HRID 1633880 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-79184d3f718c4a2398fdadd987c32f79
Source dataset
uspto-grants-2003_01
Patent number
US06504031B1

Reaction notes

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