Acetic Acid → Hexanoic acid, 6-(ethylamino)-, ethyl ester

HRID 604203Notes

Reaction equation

HRID 604203 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])(=O)[CH3:2].[BH4-].[Na+].[C:16](O)(=O)C.O>O1CCCC1>[CH2:1]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:16])=[O:11])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 13718774Methyl 6-acetamidohexanoate

Product 1

HCID 57550988Hexanoic acid, 6-(ethylamino)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude methyl 6-acetylamino-hexanoate (5.19 g) is dissolved in tetrahydrofuran (50 ml) and thereto is added sodium borohydride (5.03 g). The reaction solution is heated under reflux and thereto is added dropwise acetic acid (7.6 ml) and the mixture is heated under reflux for 1 hour and 30 minutes. To the reaction solution is added water under ice-cooling and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is dissolved in ethanol (30 ml) and thereto is added a 4N-hydrochloric acid in ethyl acetate (7.6 ml) and the mixture is stirred at room temperature overnight. To the reaction solution are added a 2N-aqueous sodium hydroxide solution and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give ethyl 6-ethylamino-hexanoate (1.74 g) as a crude product. MS (m/z): 188 [M+H]+

Workup

  1. temperatureThe reaction solution is heated
  2. temperatureunder reflux
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 1 hour and 30 minutes
  5. temperaturecooling
  6. extractionthe mixture is extracted with ethyl acetate
  7. washThe organic layer is washed with a saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe resulting residue is dissolved in ethanol (30 ml)
  11. additionis added a 4N-hydrochloric acid in ethyl acetate (7.6 ml)
  12. additionTo the reaction solution are added a 2N-aqueous sodium hydroxide solution and ethyl acetate
  13. customthe mixture is separated
  14. washthe organic layer is washed with a saturated brine
  15. dry with materialdried over magnesium sulfate
  16. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0ab29881c44b43339f74fdd850a3142a
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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