Phenethylamine → HCID 23044049, compound

HRID 2165216Notes

Reaction equation

HRID 2165216 reaction equation
[O:1]=[C:2]1[O:6][CH:5]([CH2:7][CH2:8][C:9]([OH:11])=O)[CH2:4][CH2:3]1.C1N=CN(C(N2C=NC=C2)=O)C=1.[C:24]1([CH2:30][CH2:31][NH2:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[C:24]1([CH2:30][CH2:31][NH:32][C:9](=[O:11])[CH2:8][CH2:7][CH:5]2[CH2:4][CH2:3][C:2](=[O:1])[O:6]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2221903-(5-Oxotetrahydrofuran-2-yl)propanoic acid

Product 1

HCID 23044049HCID 23044049, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,3,4,5-tetrahydro-5-oxo-2-furanpropanoic acid (7.9 g) and N,N-carbonyldiimidazole (8.1 g) in dry dichloromethane (100 ml) was stirred under nitrogen at 20° for 30 minutes and a solution of 2-phenylethylamine (6.05 g) in dry dichloromethane (20 ml) was then added. The mixture was stirred at 20° for 2 hours. The solution was washed with 2N hydrochloric acid, saturated sodium bicarbonate solution, water, dried (MgSO4), filtered and evaporated to give an oil which solidified on standing. Crystallisation from toluene gave the amide as fluffy crystals (10.4 g), mp 86°-87°.

Workup

  1. washThe solution was washed with 2N hydrochloric acid, saturated sodium bicarbonate solution, water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give an oil which
  6. customCrystallisation from toluene

Sources & evidence

ORD record
ord-193961e2780e4bf687a994b63ff2899b
Source dataset
uspto-grants-1990_07
Patent number
US04939147

Reaction notes

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