Hydrochloric Acid → HCID 44816597, compound

HRID 446204Notes

Reaction equation

HRID 446204 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:13](=[O:15])[CH3:14])[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]12[CH2:11][CH2:10][C:9]([NH:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([CH2:8][CH2:7]1)[CH2:14][C:13]2=[O:15])=[O:5])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 12522245ethyl 1-acetyl-4-oxocyclohexane-1-carboxylate

Product 1

HCID 44816597HCID 44816597, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

Toluene (310 mL) was added to 1-acetyl-4-oxocyclohexyl carboxylic acid ethyl ester (31.0 g, 146 mmol) and then the resulting mixture was stirred. To the mixture, there were added benzylamine (48.0 mL, 438 mmol) and p-toluenesulfonic acid monohydrate (251 mg, 1.32 mmol). The mixture was refluxed for 7 hours with a Dean-Stark apparatus under the dehydration conditions. The mixture was cooled to 20° C., a 3 mol/L hydrochloric acid solution (155 g) was added dropwise to the mixture and then the resulting mixture was stirred for 0.5 hours. To the mixture, there was added dropwise a 6 mol/L aqueous sodium hydroxide solution, followed by stirred for 10 minutes and the organic phase was separated. The resulting organic phase was washed twice with 155 g of a 18% aqueous ammonium chloride solution and further washed with 62 g of water. The organic phase was subjected to quantitative analysis (according to the LC technique) and as a result, the yield of the desired product was found to be 95% (the internal standard substance used was m-xylene).

Workup

  1. temperatureThe mixture was refluxed for 7 hours with a Dean-Stark apparatus under the dehydration conditions
  2. stirringthe resulting mixture was stirred for 0.5 hours
  3. stirringby stirred for 10 minutes
  4. customthe organic phase was separated
  5. washThe resulting organic phase was washed twice with 155 g of a 18% aqueous ammonium chloride solution
  6. washfurther washed with 62 g of water

Sources & evidence

ORD record
ord-b128f340b4ba49fd901b530c065b635d
Source dataset
uspto-grants-2013_07
Patent number
US08476470B2

Reaction notes

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