Potassium Carbonate → HCID 28761843, compound

HRID 571231Notes

Reaction equation

HRID 571231 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[CH2:10][NH:9][CH2:8][CH2:7]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25]>C(#N)C.C(OCC)(=O)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[CH2:10][N:9]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH2:8][CH2:7]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 64560356,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 28761843HCID 28761843, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3 g, 13.06 mmol) was suspended in acetonitrile (40 ml); potassium carbonate (3.61 g, 26.1 mmol) and methyl 2-bromoacetate (3.00 g, 19.59 mmol) were added; and the reaction mixture was stirred under microwave irradiation at 100° C. for 1 hour. Then the mixture was diluted with ethyl acetate and washed with water, brine and dried over Na2SO4. The organic layer was evaporated and the resulting crude was purified by flash chromatography on silica gel (DCM:MeOH:TEA 100:1:1) affording the title compound (2.6 g, 9.81 mmol, 75% yield). MS/ESI+ 266.1 [MH]+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. customThe organic layer was evaporated
  4. customthe resulting crude was purified by flash chromatography on silica gel (DCM:MeOH:TEA 100:1:1)

Sources & evidence

ORD record
ord-a056b96142514ca68bfd28526b70b30e
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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