1,2,3,4-Tetrahydroisoquinoline → 2-[(Oxiran-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline

HRID 1464255Notes

Reaction equation

HRID 1464255 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:17]([CH:19]1[O:21][CH2:20]1)Br>C(#N)C>[O:21]1[CH2:20][CH:19]1[CH2:17][N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 10340Sodium CarbonateHCID 18430Epibromohydrin

Product 1

HCID 167845312-[(Oxiran-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolineYield 43.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,2,3,4-tetrahydroisoquinoline (25.0 g) was dissolved in acetonitrile (100 ml) and sodium carbonate (40.0 g) and epibromohydrin (31.0 g) were added thereto and heated at reflux for 4 hours. After the resultant salt was filtered, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Waco Gel C-200, 500 g) and eluted with a mixed solvent of chloroform (99 parts)+methanol (1 part) to give 2-[1-(2,3-epoxy)propyl]-1,2,3,4-tetrahydroisoquinoline (15.6 g).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. filtrationAfter the resultant salt was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (Waco Gel C-200, 500 g)
  6. washeluted with a mixed solvent of chloroform (99 parts)+methanol (1 part)

Sources & evidence

ORD record
ord-41f8cb9b5ad2486d9bb651cd57e9f321
Source dataset
uspto-grants-1994_04
Patent number
US05304558

Reaction notes

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