Formaldehyde → 6-Methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1713077Notes

Reaction equation

HRID 1713077 reaction equation
[O:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][NH2:8])[CH3:2].[CH2:12]=O>C(O)=O>[CH3:2][O:1][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:12][NH:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 748663-Methoxyphenethylamine

Product 1

HCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To the solution of 3-methoxylphenethylamine (15.1 g, 0.1 mol) in formic acid (100 ml) at rt is added paraformaldehyde (3.0 g, 0.1 mol, 1.0 eq.). The resulting mixture is stirred at 40˜50° C. for 24 hr. After the reaction is completed, the formic acid is evaporated and the residue is diluted with water (200 ml), basified with sodium hydroxide solution (10.0N, 10.5 ml) to pH=10, and extracted with EtOAc. The combined organic layers are washed with water and brine and dried over sodium sulfate, and the solvent is removed under reduced pressure to give the title compound. MS (+VE) m/z 164.1 (M++1).

Workup

  1. customthe formic acid is evaporated
  2. additionthe residue is diluted with water (200 ml)
  3. extractionextracted with EtOAc
  4. washThe combined organic layers are washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-62d6ae6327b641b8ab79a94d8fa307ab
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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