2-Bromoethanol → HCID 67681281, compound

HRID 440506Notes

Reaction equation

HRID 440506 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]=1OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31](=[O:34])([O-])[O-].[K+].[K+].Br[CH2:38][CH2:39][OH:40]>CC(C)=O>[CH2:1]([O:8][C:9]1([O:34][CH3:31])[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][N:15]([CH2:38][CH2:39][OH:40])[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][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 22406704HCID 22406704, compound

Product 1

HCID 67681281HCID 67681281, 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 (2.83 g, liberated from the hydrobromide salt prepared in a similar manner to that described in Example RC14), acetone (40 ml), anhydrous potassium carbonate (5.5 g) and 2-bromoethanol (3.6 ml) was heated under reflux for 18 hours. The mixture was filtered, the solids washed with acetone, and the filtrate solvent removed in vacuo to give 7-benzyloxy-1-[1-(2-chlorophenyl)cyclopropyl]-2-(2-hydroxyethyl)-7-methoxy-1,2,3,4-tetrahydroisoquinoline as an oil.

Workup

  1. customprepared in a similar manner to that
  2. temperaturewas heated
  3. temperatureunder reflux for 18 hours
  4. filtrationThe mixture was filtered
  5. washthe solids washed with acetone
  6. customthe filtrate solvent removed in vacuo

Sources & evidence

ORD record
ord-162b57d66fa84b49be0513ff1489eeb6
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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