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

HRID 1840730Notes

Reaction equation

HRID 1840730 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. Then, the mixture was heated under reflux for 4 hours. After separating salts in the mixture by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Wako gel C-200, 500 g), and then was eluted with a mixed solvent of 99 parts of chloroform and 1 part of methanol to obtain 2-{1-(2,3-epoxy) propyl}-1,2,3,4-tetrahydroisoquinoline (15.6 g).

Workup

  1. temperatureThen, the mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customAfter separating salts in the mixture
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (Wako gel C-200, 500 g)
  7. washwas eluted with a mixed solvent of 99 parts of chloroform and 1 part of methanol

Sources & evidence

ORD record
ord-e8f45d1df31348ecb177b82b5897c300
Source dataset
uspto-grants-2004_01
Patent number
US06683083B1

Reaction notes

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