Benzenepropanoic acid → Benzenepropanamide, N-[3-(1H-imidazol-1-yl)propyl]-

HRID 1589186Notes

Reaction equation

HRID 1589186 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O1CCCC1.[N:29]1([CH2:34][CH2:35][CH2:36][NH2:37])[CH:33]=[CH:32][N:31]=[CH:30]1>O>[N:29]1([CH2:34][CH2:35][CH2:36][NH:37][C:9](=[O:11])[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:33]=[CH:32][N:31]=[CH:30]1

Participants

6

Reactant 4

HCID 107Benzenepropanoic acidHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 3425920Benzenepropanamide, N-[3-(1H-imidazol-1-yl)propyl]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.50 g. of 3-phenylpropionic acid, 1.62 g. of 1,1'-carbonyldiimidazole, and 40 ml. of tetrahydrofuran was stirred for 3 hours and 2.0 g. of 1H-imidazole-1-propanamine was added. The mixture was stirred for 18 hours, 5 ml. of water was added, and the reaction mixture was heated at reflux temperature for 30 minutes. The mixture was concentrated and 10 ml. 1N sodium hydroxide and 100 ml. of methylene chloride were added. The layers were separated and the organic layer was washed with water, dried over magnesium sulfate, and concentrated. The desired product was obtained as an oil, which was converted to the fumarate salt, m.p. 90°-92° C.

Workup

  1. additionA mixture of 1.50 g
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux temperature for 30 minutes
  4. concentrationThe mixture was concentrated
  5. additionof methylene chloride were added
  6. customThe layers were separated
  7. washthe organic layer was washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-410357067c9743d69328c7a186ac6706
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

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