Ethylamine hydrochloride → N-Ethyl-2-(4-iodo-phenyl)-propionamide

HRID 330813Notes

Reaction equation

HRID 330813 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH3:13][CH2:14][N:15](C(C)C)C(C)C.Cl.C(N)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:14]([NH:15][C:9](=[O:11])[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=1)[CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 152255732-(4-Iodophenyl)propanoic acid

Product 1

HCID 66693450N-Ethyl-2-(4-iodo-phenyl)-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.97 g (7.14 mmol) 2-(4-Iodo-phenyl)-propionic acid (111.1) and 1.25 mL (7.14 mmol) DIPEA are added to 582 mg (7.14 mmol) ethylamine hydrochlorid in 70 mL DCM. 1.64 g (8.57 mmol) N-(3-Dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and 194 mg (1.43 mmol) 1-hydroxy-7-azabenotriazole are added at 0° C. Subsequently, cooling is removed and the mixture is stirred for 20 h at rt. After that time, the mixture is washed with water and brine, dried over sodium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silicia gel; heptane:EtOAc 50:50).

Workup

  1. temperatureSubsequently, cooling
  2. customis removed
  3. washAfter that time, the mixture is washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. customthe solvent is evaporated
  6. customThe residue is purified by column chromatography (silicia gel; heptane:EtOAc 50:50)

Sources & evidence

ORD record
ord-a3e0281aa7624959a4a5400401d16364
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

Loading…