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

HRID 1399898Notes

Reaction equation

HRID 1399898 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
25 °C

Procedure

To a solution of 1,2,3,4-tetrahydroisoquinoline (15 g, 0.11 mol) in MeCN (100 mL) was added K2CO3 (30.7 g, 0.23 mol) at 0° C. 2-(Bromomethyl)oxirane (17 g, 0.12 mol) was added to the reaction mixture over a period of 1 h. The mixture was then warmed and stirred at 25° C. for 16 h. At this point the solid was removed by filtration and washed with MeCN. The filtrate was concentrated and the residue used for next step without further purification (17 g Yield 78%). LCMS (m/z): 190.1 [M+H]+.

Workup

  1. temperatureThe mixture was then warmed
  2. customAt this point the solid was removed by filtration
  3. washwashed with MeCN
  4. concentrationThe filtrate was concentrated
  5. customthe residue used for next step without further purification (17 g Yield 78%)

Sources & evidence

ORD record
ord-211caf7d23fc467e87fddd692b258926
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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