Hydrochloric Acid → methyl 4-(N-benzylamino)-1-methyl-1-cyclohexanecarboxylate

HRID 2225482Notes

Reaction equation

HRID 2225482 reaction equation
Cl.CO.[CH2:4]([NH2:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:12][C:13]1([C:20]([O:22][CH3:23])=[O:21])[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.C([BH3-])#N.[Na+].Cl>CO>[CH2:4]([NH:11][CH:16]1[CH2:17][CH2:18][C:13]([CH3:12])([C:20]([O:22][CH3:23])=[O:21])[CH2:14][CH2:15]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 12568255Methyl 1-methyl-4-oxocyclohexane-1-carboxylateHCID 21893726Hydrochloride methanol

Product 1

HCID 19004646methyl 4-(N-benzylamino)-1-methyl-1-cyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5N hydrochloric acid-methanol was added to a solution of 19.6 ml of benzylamine in 75 ml of methanol under ice-cooling, neutralizing the solution. Then, 5.1 g of methyl 1-methyl-4-oxo-1-cyclohexanecarboxylate and 1.13 g of sodium cyanoborohydride were added to the mixture solution. The solution was reacted at room temperature for 26 hours. After reaction, concentrated hydrochloric acid was added to the reaction solution, adjusting the pH value to 2 or less. The solution was washed three times with 30 ml of methylene chloride. Further, a 2N aqueous sodium hydroxide solution was added to the aqueous layer formed, adjusting the pH value to 10 or more. The solution was extracted three times with 30 ml of ethyl acetate. The organic layer obtained was washed twice with an aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed in vacuo. The oily substance, thus obtained, was subjected to column chromatography using 50 g of silica gel. From the fraction eluted with hexane and ethyl acetate=4:1, the solvent was removed in vacuo, yielding 3.1 g of methyl 4-(N-benzylamino)-1-methyl-1-cyclohexanecarboxylate as a colorless oil, which had the following physiochemical properties:

Workup

  1. temperaturecooling
  2. customThe solution was reacted at room temperature for 26 hours
  3. additionwas added to the reaction solution
  4. washThe solution was washed three times with 30 ml of methylene chloride
  5. additionFurther, a 2N aqueous sodium hydroxide solution was added to the aqueous layer
  6. customformed
  7. extractionThe solution was extracted three times with 30 ml of ethyl acetate
  8. customThe organic layer obtained
  9. washwas washed twice with an aqueous sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent was removed in vacuo
  12. customThe oily substance, thus obtained
  13. washFrom the fraction eluted with hexane and ethyl acetate=4:1
  14. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f19a9da3d6be49c78e53b0fd768cac86
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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