Triethylamine → 3-(4-Methoxyphenyl)propanamide

HRID 736855Notes

Reaction equation

HRID 736855 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])C(O)=O)=[CH:5][CH:4]=1.C([N:16]([CH2:19]C)CC)C.ClC(OCC)=[O:23].[NH4+].[OH-]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:13][C:19]([NH2:16])=[O:23])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 257576p-Methoxyphenylpropionic acid

Product 1

HCID 6979553-(4-Methoxyphenyl)propanamideYield 95.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(4-methoxyphenyl)propionic acid (20.0 mg, 0.11 mmol) prepared in Reference Synthetic Example 2 was dissolved in tetrahydrofuran (500 μl) in nitrogen atmosphere, and triethylamine (17 μl, 0.12 mmol) and ethyl chloroformate (11 μl, 0.12 mmol) were dropwise added under cooling with ice, followed by stirring for 15 minutes. A 28% ammonia aqueous solution was dropwise added, followed by stirring for 5 minutes, and the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2 to 1:2) to give the desired compound 3-(4-methoxyphenyl)propionic acid amide (18.9 mg, 95%) as colorless needle crystals.

Workup

  1. additionwere dropwise added
  2. temperatureunder cooling with ice
  3. stirringby stirring for 5 minutes
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2 to 1:2)

Sources & evidence

ORD record
ord-a9e2fae14fb341a5a6aff73b11865638
Source dataset
uspto-grants-2009_09
Patent number
US07595415B2

Reaction notes

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