Ethanol → HCID 67538611, compound

HRID 2383070Notes

Reaction equation

HRID 2383070 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:16](=[O:27])[CH2:17][NH:18][CH2:19][C:20]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH:7]2[CH:13]([CH3:15])[CH3:14].CCO.C(N(CC)CC)C.[C:38]([OH:43])(=[O:42])[C:39]([OH:41])=[O:40]>[Pd].C(OCC)C>[C:38]([OH:43])(=[O:42])[C:39]([OH:41])=[O:40].[CH:13]([CH:7]1[C:8]2[C:3](=[CH:2][CH:11]=[CH:10][C:9]=2[CH3:12])[CH2:4][CH2:5][N:6]1[C:16](=[O:27])[CH2:17][NH:18][CH2:19][C:20]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 702EthanolHCID 971Oxalic AcidHCID 8471TriethylamineHCID 67538542HCID 67538542, compound

Product 1

HCID 67538611HCID 67538611, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-({[2-(5-bromo-1-isopropyl-8-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino}methyl)cyclohexanol (0.14 g), EtOH (10 mL), triethylamine (0.05 mL), and 10% palladium-supported carbon (10 mg) was stirred under a hydrogen atmosphere for 6 hours. The reaction liquid was filtered and the solvent was evaporated. A 1 M NaOH aqueous solution was added to the resulting residue, followed by extraction with chloroform. The organic layer was dried over magnesium sulfate and then the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (chloroform-MeOH). The resulting residue was dissolved in 2-propanol (0.8 mL). To the reaction liquid were added oxalic acid (23 mg) and diethyl ether (5 mL) and the precipitated solid was collected by filtration and dried to obtain 1-({[2-(1-isopropyl-8-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino}methyl)cyclohexanol oxalate (0.066 g).

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. customthe solvent was evaporated
  4. additionA 1 M NaOH aqueous solution was added to the resulting residue
  5. extractionfollowed by extraction with chloroform
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)
  9. dissolutionThe resulting residue was dissolved in 2-propanol (0.8 mL)
  10. customTo the reaction liquid
  11. filtrationthe precipitated solid was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-f0a870ba6e6c48b59ce666fb2e38524b
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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