Potassium Iodide → HCID 59396427, compound

HRID 2383069Notes

Reaction equation

HRID 2383069 reaction equation
[CH:1]1([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:17](=[O:27])[CH2:18][NH:19][CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:29][CH2:30][OH:31].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH:1]1([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:17](=[O:27])[CH2:18][N:19]([CH2:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[CH2:29][CH2:30][OH:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 67538211HCID 67538211, compound

Product 1

HCID 59396427HCID 59396427, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-N-(cyclohexylmethyl)-2-oxoethanamine (296 mg) was dissolved in acetonitrile (10 mL). To the reaction liquid were added 2-bromoethanol (400 mg), potassium carbonate (555 mg), and potassium iodide (133 mg), followed by stirring under heating at reflux for 16 hours. Thereafter, the solvent was evaporated and water was added to the reaction liquid, followed by extraction with chloroform. The extract was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (chloroform-MeOH) to obtain 2-{[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl](cyclohexylmethyl)amino}ethanol (155 mg).

Workup

  1. customTo the reaction liquid
  2. temperatureunder heating
  3. temperatureat reflux for 16 hours
  4. customThereafter, the solvent was evaporated
  5. additionwater was added to the reaction liquid
  6. extractionfollowed by extraction with chloroform
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated
  10. customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)

Sources & evidence

ORD record
ord-d6d05d2cac1142f3a66fcc4631bb545e
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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