Methanol → N-heptyl-N-ethyl(6-hydroxy)hexanamide

HRID 36147Notes

Reaction equation

HRID 36147 reaction equation
[CH2:1]([N:8]([CH2:19][CH3:20])[C:9](=[O:18])[CH2:10][CH2:11][CH2:12][CH2:13][C:14](OC)=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[BH4-].[Na+].CO>C(O)(C)(C)C>[CH2:1]([N:8]([CH2:19][CH3:20])[C:9](=[O:18])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86748668N-heptyl-N-ethyladipamic acid, methyl ester

Product 1

HCID 22407916N-heptyl-N-ethyl(6-hydroxy)hexanamideYield 35.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of a solution of 3.1 gms of the N-heptyl-N-ethyladipamic acid, methyl ester in 40 ml of tert-butanol and 800 mg of sodium borohydride is heated to reflux, following which 7.8 ml of methanol is added dropwise. The reaction mixture is stirred at reflux for 18 hours and then partitioned between water and CH2Cl2. After separation, the organic layer is dried over MgSO4, filtered, and concentrated under vacuum. The residue obtained is flash chromatographed on normal phase silica gel with a 4/1 ratio of hexane and ethyl acetate to yield 1.0 gms of N-heptyl-N-ethyl(6-hydroxy)hexanamide.

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. additionis added dropwise
  4. temperatureat reflux for 18 hours
  5. custompartitioned between water and CH2Cl2
  6. customAfter separation
  7. dry with materialthe organic layer is dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue obtained
  11. customchromatographed on normal phase silica gel with a 4/1 ratio of hexane and ethyl acetate

Sources & evidence

ORD record
ord-6a455df6206d4f0fa050d33537601b1c
Source dataset
uspto-grants-1995_05
Patent number
US05412137

Reaction notes

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