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

HRID 2202075Notes

Reaction equation

HRID 2202075 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.[K+].[K+].Br[CH2:18][CH:19]1[CH2:21][O:20]1>CC#N>[O:20]1[CH2:21][CH:19]1[CH2:18][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 11430Potassium CarbonateHCID 18430Epibromohydrin

Product 1

HCID 167845312-[(Oxiran-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolineYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
21 °C

Procedure

To a stirring solution of 1,2,3,4-tetrahydroisoquinoline (15 g, 0.11 mol) in MeCN (100 mL) at 0° C. was added K2CO3 (30.7 g, 0.23 mol), then 2-(bromomethyl) oxirane (17 g, 0.12 mol) added slowly over a period of 1 h. After the addition the solution was stirred at 21° C. for 12 h. The resulting solid was then removed by filtration and washed with MeCN and the combined organic filtrate was concentrated under reduced pressure to give the crude product. This residue was used into next step without further purification (17 g, Yield: 78%). LCMS (m/z): 190.1 (M+1).

Workup

  1. additionAfter the addition the solution
  2. customThe resulting solid was then removed by filtration
  3. washwashed with MeCN
  4. concentrationthe combined organic filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-10399ac78ea04b3799b59cf2e5c64012
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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