Ethyl cyclohexanoate → HCID 23157133, compound

HRID 2265138Notes

Reaction equation

HRID 2265138 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[CH2:12]([NH2:15])[C:13]#[CH:14]>O.O.[Na+].Cl[Au-](Cl)(Cl)Cl.C(O)C>[N:15]1[C:1]2[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][C:2]=2[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 18686Ethyl cyclohexanoateHCID 239041Propargylamine

Product 1

HCID 23157133HCID 23157133, compound

Reagents, catalysts & solvents 2

HCID 18949434Sodium tetrachloroaurate dihydrateCatalystHCID 702EthanolSolvent2×

Procedure

At 60° C., ethanol (250 mL) solution of 500 g of ethyl 4-cyclohexanecarboxylate is added to ethanol (2.5 L) solution of 376 mL of propargylamine and 29.2 g of sodium tetrachloroaurate(III) dihydrate, and stirred overnight with reflux. The insoluble solid substance was removed through filtration through Celite, and the solvent was evaporated off under reduced pressure. The residue was separated and purified through silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain 555 g of ethyl 5,6,7,8-tetrahydroquinoline-6-carboxylate as a brown oily substance. The compound contained impurities.

Workup

  1. temperaturewith reflux
  2. customThe insoluble solid substance was removed through filtration through Celite
  3. customthe solvent was evaporated off under reduced pressure
  4. customThe residue was separated
  5. custompurified through silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-a40a67b9dcb0485d9e742f887b3cc8c8
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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