Triethylamine → HCID 70587025, compound

HRID 2052476Notes

Reaction equation

HRID 2052476 reaction equation
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(N(CC)CC)C.ClC(OCC)=O.[NH2:34][CH:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:37][CH2:36]1>C(Cl)Cl>[CH:35]1([NH:34][C:1](=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 123445(+-)-1-AminoindanHCID 5280450Linoleic Acid

Product 1

HCID 70587025HCID 70587025, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.0 g linoleic acid in 250 ml methylenechloride cooled to -20° is added 2.5 g triethylamine, and then dropwise 2.7 g ethyl chloroformate. The reaction mixture is allowed to come to room temperature and then stirred 2 hours. To the reaction mixture is then added, dropwise, 3.4 g 1-aminoindan, and the reaction mixture then stirred for 16 hours. The reaction mixture is then extracted several times with 2 N hydrochloric acid, then with 2 N aqueous sodium hydroxide solution, washed well with saturated aqueous sodium chloride, dried over anh. sodium sulphate, filtered and the filtrate evaporated i.v. to dryness. The resulting residue is rapidly filtered over silica gel, with methylene chloride as solvent. The necessary fractions indicated to contain reaction product by thin layer chromatography of samples are pooled and solvent removed by evaporation under vacuum to give title product as a viscous oil, characterized by NMR (in CDCl3); triplet at 5.15 ppm (4 protons) and doublet at 6.4 ppm (1 proton).

Workup

  1. customto come to room temperature
  2. additionTo the reaction mixture is then added
  3. extractionThe reaction mixture is then extracted several times with 2 N hydrochloric acid
  4. washwith 2 N aqueous sodium hydroxide solution, washed well with saturated aqueous sodium chloride
  5. dry with materialdried over anh. sodium sulphate
  6. filtrationfiltered
  7. customthe filtrate evaporated i.v
  8. filtrationThe resulting residue is rapidly filtered over silica gel, with methylene chloride as solvent
  9. customreaction product by thin layer chromatography of samples
  10. customsolvent removed by evaporation under vacuum

Sources & evidence

ORD record
ord-5b6ba9b5343a49e9a3ad9ccc78a08475
Source dataset
uspto-grants-1980_01
Patent number
US04185118

Reaction notes

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