3-Phenylpropylamine → N-(3-Phenylpropyl)-1H-Imidazole-1-Carboxamide

HRID 719751Notes

Reaction equation

HRID 719751 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].[C:13]1([CH2:19]CCN)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[C:13]1([CH2:19][CH2:11][CH2:12][NH:8][C:1]([N:3]2[CH:7]=[CH:6][N:5]=[CH:4]2)=[O:2])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 162593-Phenylpropylamine2×HCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 11368189N-(3-Phenylpropyl)-1H-Imidazole-1-Carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1,1′-carbonyldiimidazole (33.00 g, 0.203 mol) in THF (100 mL) at room temperature under N2, was added 3-phenylpropylamine (25.00 g, 0.185 mol) in THF (50 mL), dropwise. The reaction mixture became clear during the addition of the 3-phenylpropylamine. After completion of the addition, the clear solution was stirred for 30 min at room temperature and then quenched with water (150 mL) and ethyl acetate (200 mL). The layers were separated and the organic layer washed with water (150 mL), brine (150 mL), and dried with Na2SO4. The solvents were removed in vacuo to yield a white wax-like solid.

Workup

  1. additionAfter completion of the addition
  2. customquenched with water (150 mL) and ethyl acetate (200 mL)
  3. customThe layers were separated
  4. washthe organic layer washed with water (150 mL), brine (150 mL)
  5. dry with materialdried with Na2SO4
  6. customThe solvents were removed in vacuo
  7. customto yield a white wax-like solid

Sources & evidence

ORD record
ord-75d22564a11740d598914134d8219280
Source dataset
uspto-grants-2006_11
Patent number
US07132544B2

Reaction notes

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