Potassium Carbonate → HCID 25067546, compound

HRID 2383067Notes

Reaction equation

HRID 2383067 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C@@H:6]1[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:28][CH2:29][C:30]1([OH:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:15]1([C@H:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13][CH2:14][N:5]2[C:3](=[O:4])[CH2:2][NH:28][CH2:29][C:30]2([OH:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)HCID 67536844HCID 67536844, compound

Product 1

HCID 25067546HCID 25067546, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

(1S)-2-(chloroacetyl)-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline (4.496 g) was dissolved in acetonitrile (100 mL). To the mixture were added potassium carbonate (6.25 g), tetra-n-butylammoniumiodide (679 mg), and 1-(aminomethyl)cyclohexanol hydrochloride (4.50 g), followed by stirring at 60° C. for 6 hours. Thereafter, the solvent was evaporated and water was added to the reaction mixture, 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 to obtain 1-[({2-[(1S)-1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl]-2-oxoethyl}amino)methyl]cyclohexanol (3.02 g).

Workup

  1. customThereafter, the solvent was evaporated
  2. additionwater was added to the reaction mixture
  3. extractionfollowed by extraction with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9bd99bf26d774eeb92cd58924fcfac23
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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