Potassium Carbonate → 6-Hydroxy-2-(3-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

HRID 2413491Notes

Reaction equation

HRID 2413491 reaction equation
Br.[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Cl.C(=O)([O-])[O-].[K+].[K+]>>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([CH2:18][C:17]1[CH:20]=[CH:21][CH:22]=[C:15]([O:14][CH3:13])[CH:16]=1)[CH2:7][CH2:6]2

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 699943-Methoxybenzyl chlorideHCID 133617991,2,3,4-Tetrahydroisoquinolin-6-ol--hydrogen bromide (1/1)

Product 1

HCID 133618016-Hydroxy-2-(3-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

Procedure

4.3 g of 6-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide, 3.1 g of 3-methoxybenzyl chloride and 2.8 g of finely powdered potassium carbonate are first stirred at room temperature for 2 hours and then at 80° C. for 5 hours. After cooling, the solvent is removed in vacuo, the residue is taken up with water/methylene chloride, and the organic phase is again shaken with water and dried over magnesium sulfate. After evaporation in a rotary evaporator, a yellow oil remains, and this crystallizes after trituration with ethyl acetate.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is removed in vacuo
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation
  5. customin a rotary evaporator
  6. customthis crystallizes after trituration with ethyl acetate

Sources & evidence

ORD record
ord-50943005634a4c10a4467382b5bcd4a1
Source dataset
uspto-grants-1988_01
Patent number
US04717724

Reaction notes

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