Triethylamine → N-[2-(2-ethoxyphenoxy)ethyl]-3-(4-fluorobenzoyl)-propionamide

HRID 1414432Notes

Reaction equation

HRID 1414432 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=O)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[CH2:28]([O:30][C:31]1[CH:40]=[CH:39][CH:38]=[CH:37][C:32]=1[O:33][CH2:34][CH2:35][NH2:36])[CH3:29]>O1CCCC1>[CH2:28]([O:30][C:31]1[CH:40]=[CH:39][CH:38]=[CH:37][C:32]=1[O:33][CH2:34][CH2:35][NH:36][C:10](=[O:12])[CH2:9][CH2:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:14][CH:13]=1)[CH3:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 1013593-(4-Fluorobenzoyl)propionic acidHCID 53030422-(2-Ethoxyphenoxy)ethylamine

Product 1

HCID 21487435N-[2-(2-ethoxyphenoxy)ethyl]-3-(4-fluorobenzoyl)-propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 10.4 g of 3-(4-fluorobenzoyl)propionic acid and 6.0 g of triethylamine in 120 ml of tetrahydrofuran was added dropwise 6.0 g of ethyl chloroformate at a temperature below 0° C. After stirring was continued for half an hour, to the mixture was added a solution of 9.6 g of 2-(2-ethoxyphenoxy)ethylamine in 10 ml of tetrahydrofuran. Further stirring was continued at room temperature for 4 hours. The reaction mixture was filtered and the filtrate was concentrated to a residue under reduced pressure. The residue was recrystallized from benzene-hexane to give N-[2-(2-ethoxyphenoxy)ethyl]-3-(4-fluorobenzoyl)-propionamide melting at 98° - 100° C.

Workup

  1. waitwas continued for half an hour, to the mixture
  2. stirringFurther stirring
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated to a residue under reduced pressure
  5. customThe residue was recrystallized from benzene-hexane

Sources & evidence

ORD record
ord-e78a834b8f654db5b659557e3d3e70a7
Source dataset
uspto-grants-1977_01
Patent number
US04001312

Reaction notes

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