Acetic Acid → HCID 178464368, compound

HRID 78867Notes

Reaction equation

HRID 78867 reaction equation
[C:1]([NH:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8][CH2:7]1)(=O)[CH3:2].[BH4-].[Na+].C(O)(=O)C.O>O1CCCC1>[CH2:1]([NH:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8][CH2:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 178471792HCID 178471792, compound

Product 1

HCID 178464368HCID 178464368, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl trans-{4-[(acetylamino)methyl]cyclohexyl}acetate (1.19 g, 4.93 mmol) was dissolved in tetrahydrofuran (25 mL), the solution was added with sodium borohydride (932 mg, 24.66 mmol), the mixture was added dropwise with a solution of acetic acid (1.48 g, 24.66 mmol) in tetrahydrofuran (25 mL) over 1 hour under reflux by heating, and the mixture was stirred at the same temperature for 6 hours. The reaction mixture was added dropwise with water with stirring under ice cooling, and the reaction was thereby quenched. The reaction mixture was made alkaline with 2 M aqueous sodium hydroxide, and extracted with ethyl acetate, and the organic layer was successively washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the resulting crude product of ethyl trans-{4-[(ethylamino)methyl]cyclohexyl}acetate was dissolved in ethanol (20 mL), the solution was added with 4 M hydrochloric acid in ethyl acetate (6 mL), and the mixture was stirred for 12 hours. The reaction mixture was diluted with ethyl acetate, and the organic layer was successively washed with 2 M sodium hydroxide, water, and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain the objective ethyl trans-{4-[(ethylamino)methyl]cyclohexyl}acetate as pale brown oil (1.12 g, 99%).

Workup

  1. temperatureunder reflux
  2. temperatureby heating
  3. stirringwith stirring under ice cooling
  4. customthe reaction was thereby quenched
  5. extractionextracted with ethyl acetate
  6. washthe organic layer was successively washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. dissolutionthe resulting crude product of ethyl trans-{4-[(ethylamino)methyl]cyclohexyl}acetate was dissolved in ethanol (20 mL)
  10. additionthe solution was added with 4 M hydrochloric acid in ethyl acetate (6 mL)
  11. stirringthe mixture was stirred for 12 hours
  12. additionThe reaction mixture was diluted with ethyl acetate
  13. washthe organic layer was successively washed with 2 M sodium hydroxide, water, and saturated brine
  14. dry with materialdried over anhydrous sodium sulfate
  15. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6183cdca66dc47f2ac68e5e6712f6df8
Source dataset
uspto-grants-2014_09
Patent number
US08841478B2

Reaction notes

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