Potassium Carbonate → HCID 22406810, compound

HRID 440505Notes

Reaction equation

HRID 440505 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][NH:15][CH:16]2[C:19]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[CH2:21][CH2:20]2)=[CH:11][C:10]=1[O:29][CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:37][O:38][CH2:39][CH2:40]Br>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][N:15]([CH2:40][CH2:39][O:38][CH3:37])[CH:16]2[C:19]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[CH2:20][CH2:21]2)=[CH:11][C:10]=1[O:29][CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 809722-Bromoethyl methyl ether2×HCID 22406704HCID 22406704, compound

Product 1

HCID 22406810HCID 22406810, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7-benzyloxy-1-[1-(2-chlorophenyl)cyclopropyl]-6-methoxy-1,2,3,4-tetrahydroisoquinoline (2.1 g, free base liberated from the hydrobromide salt prepared in a similar manner to that described in Example RC14), acetone (30 ml), anhydrous potassium carbonate (1.6 g) and 2-methoxyethyl bromide (2.1 g) was heated under reflux for 6 hours. After a further 16 hours at ambient temperature, potassium carbonate (3 g) and 2-methoxyethyl bromide (2.22 g) were added, and heating continued for 6 hours. The mixture was filtered, the residue washed with acetone, and solvent removed from the filtrate in vacuo to yield 7-benzyloxy-1-[1-(2-chlorophenyl)cyclopropyl]-6-methoxy-2-(2-methoxyethyl)-1,2,3,4-tetrahydroisoquinoline as an oil.

Workup

  1. customprepared in a similar manner to that
  2. temperaturewas heated
  3. temperatureunder reflux for 6 hours
  4. temperatureheating
  5. waitcontinued for 6 hours
  6. filtrationThe mixture was filtered
  7. washthe residue washed with acetone, and solvent
  8. customremoved from the filtrate in vacuo

Sources & evidence

ORD record
ord-bfa54b476043415b955fa405ccc0f7ef
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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