Water → HCID 59396683, compound

HRID 2383071Notes

Reaction equation

HRID 2383071 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:23])[CH2:18][NH:19][CH2:20][CH2:21][OH:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:24]1[C:26]2([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:25]1.O>CCO>[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:23])[CH2:18][N:19]([CH2:25][C:26]2([OH:24])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:20][CH2:21][OH:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 91001-Oxaspiro[2.5]octaneHCID 59396477HCID 59396477, compound

Product 1

HCID 59396683HCID 59396683, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-{[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino}ethanol (342 mg) was dissolved in EtOH (5 mL). 1-oxaspiro[2.5]octane (363 mg) and water (5 mL) were added thereto, followed by stirring under heating at reflux for 2 days. 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 1-({[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl](2-hydroxyethyl)amino}methyl)cyclohexanol (346 mg).

Workup

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

Sources & evidence

ORD record
ord-1caffac058e84b06a0020f3d7a6c6a3a
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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