Hydrochloric Acid → 6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 1784408Notes

Reaction equation

HRID 1784408 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][NH2:8].[CH2:12]=O.[ClH:14]>O>[ClH:14].[CH3:1][O:2][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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 748663-Methoxyphenethylamine

Product 1

HCID 29203356-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 3-methoxyphenethylamine (50.4 g, 0.33 mol. 1.0 eq) in water (40 mL) was added 37% aqueous formaldehyde solution (27.5 mL, 1.1 eq) and stirring continued for 20 min. Concentrated HCl (80 mL) was added and the mixture heated at reflux for 1 h. After cooling to room temperature the mixture was evaporated to dryness. The residue was recrystallised from acetone, affording the desired product as a white solid (60.1 g, 90%) which was used without further purification for the next step. MH+ 164.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 h
  3. customwas evaporated to dryness
  4. customThe residue was recrystallised from acetone

Sources & evidence

ORD record
ord-50686108a18240839b80a372583cce2c
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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