Ethanol → N-(heptan-4-yl)-4-(2-methoxyethoxy)-3-methylbenzamide

HRID 339350

Reaction equation

HRID 339350 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])=[O:9])=[CH:6][C:5]=1[CH3:20].Cl[CH:22]([OH:24])[CH3:23].[CH2:25](O)C>>[CH3:17][CH2:16][CH2:15][CH:11]([NH:10][C:8](=[O:9])[C:7]1[CH:18]=[CH:19][C:4]([O:3][CH2:23][CH2:22][O:24][CH3:25])=[C:5]([CH3:20])[CH:6]=1)[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 126390351-Chloroethan-1-olHCID 575277684-hydroxy-3-methyl-N-(1-propyl-butyl)-benzamide

Product 1

HCID 57527906N-(heptan-4-yl)-4-(2-methoxyethoxy)-3-methylbenzamideYield 39%

Conditions

Temperature
80 °C

Procedure

Potassium hydroxide (4 mmol) was dissolved in ethanol (5 mL) and heated at 80° C. 4-hydroxy-3-methyl-N-(1-propyl-butyl)-benzamide (example 58) (1 mmol) was added into the solution followed by chloroethanol (3 mmol). The reaction was stirred overnight at 80° C. The reaction mixture was concentrated down and dissolved in 5% citric acid. The mixture was stirred for 1 hour. The aqueous mixture was extracted three times with ethyl acetate. The combined ethyl acetate was washed with water and dried down over sodium sulfate. The organic layer was concentrated down and purified by HPLC to yield 39% of N-(heptan-4-yl)-4-(2-methoxyethoxy)-3-methylbenzamide. MS (M+H, 308.25).

Workup

  1. concentrationThe reaction mixture was concentrated down
  2. dissolutiondissolved in 5% citric acid
  3. stirringThe mixture was stirred for 1 hour
  4. extractionThe aqueous mixture was extracted three times with ethyl acetate
  5. washThe combined ethyl acetate was washed with water
  6. dry with materialdried down over sodium sulfate
  7. concentrationThe organic layer was concentrated down
  8. custompurified by HPLC

Sources & evidence

ORD record
ord-57afbe97652f466dbe71c191c0288561
Source dataset
uspto-grants-2014_11
Patent number
US08895050B2

Linked notes

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