Acetic Acid → HCID 15380922, compound

HRID 610772Notes

Reaction equation

HRID 610772 reaction equation
[H-].[H-].C[CH2-].C[CH2-].[Na+].[Al+3].[CH:9]1([NH2:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C[O:17][C:18](=O)[CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34].C(O)(=O)C>C1(C)C=CC=CC=1>[CH:9]1([NH:15][C:18](=[O:17])[CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7965CyclohexylamineHCID 87331Aluminium sodium hydride ethan-1-ide (1/1/2/2)HCID 15380921HCID 15380921, compound

Product 1

HCID 15380922HCID 15380922, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
110 °C

Procedure

A solution of sodium diethyldihydroaluminate (4.44 ml, 8.9 mmole) in a concentration of 2 moles per liter in toluene, is added to a solution of cyclohexylamine (1.76 g, 2.03 ml, 18 mmole) in anhydrous toluene (60 ml). The reaction mixture is heated to 110° C. for 1 hour, then a solution of methyl-5-[benzyl{2-(2-methoxyphenoxy)ethyl}amino]pentanoate (6 g, 16 mmole) in toluene (25 ml) is added dropwise. The mixture is heated under reflux for 3 hours and left for 18 hours at 20° C., then neutralised with a 10% solution of acetic acid. The organic phase is extracted then washed successively with a saturated solution of sodium hydrogen carbonate then with water. After drying over magnesium sulfate and evaporation of the solvents under reduced pressure, the product is purified by flash chromatography over silica gel in a mixture of ethyl acetate/heptane (2/1). 3.3 g (47%) of the desired product are obtained in the form of an oil.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. extractionThe organic phase is extracted
  4. washthen washed successively with a saturated solution of sodium hydrogen carbonate
  5. dry with materialAfter drying over magnesium sulfate and evaporation of the solvents under reduced pressure
  6. customthe product is purified by flash chromatography over silica gel in a mixture of ethyl acetate/heptane (2/1)

Sources & evidence

ORD record
ord-770edc398db1457b94fddc89bc2351fa
Source dataset
uspto-grants-1999_12
Patent number
US05998666

Reaction notes

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