Triethylamine → N-[2-(3-cyanophenoxy)ethyl]-4-isopropylbenzamide

HRID 747673Notes

Reaction equation

HRID 747673 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.Cl.[NH2:43][CH2:44][CH2:45][O:46][C:47]1[CH:48]=[C:49]([CH:52]=[CH:53][CH:54]=1)[C:50]#[N:51]>ClCCl.O>[C:50]([C:49]1[CH:48]=[C:47]([CH:54]=[CH:53][CH:52]=1)[O:46][CH2:45][CH2:44][NH:43][C:8](=[O:10])[C:7]1[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:12][CH:11]=1)#[N:51]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 108204-Isopropylbenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22645198210963-99-8

Product 1

HCID 68836070N-[2-(3-cyanophenoxy)ethyl]-4-isopropylbenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

283 mg (1.73 mmol) of 4-isopropylbenzoic acid was dissolved in 10 ml of dichloromethane. 1.2 ml (8.65 mmol) of triethylamine, 363 mg (1.90 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 256 mg (190 mmol) of 1-hydroxybenzotriazole and 342 mg (1.24 mmol) of 3-(2-aminoethoxy)benzonitrile hydrochloride were added to the solution, and they were stirred for 18 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution successively, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customThe reaction liquid
  2. extractionAfter the extraction with ethyl acetate
  3. washthe organic layer was washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-26d9da943dfb495398593362093a070e
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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