Tetrahydrofuran → 4-Fluoro-N-[3-(1H-imidazol-1-yl)propyl]benzeneacetamide

HRID 1589182Notes

Reaction equation

HRID 1589182 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O1CCCC1.Cl.Cl.[N:31]1([CH2:36][CH2:37][CH2:38][NH2:39])[CH:35]=[CH:34][N:33]=[CH:32]1>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:39][CH2:38][CH2:37][CH2:36][N:31]2[CH:35]=[CH:34][N:33]=[CH:32]2)=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 98372-(4-Fluorophenyl)acetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 122509693-(Imidazole-1-yl)-propylamine Dihydrochloride

Product 1

HCID 135889554-Fluoro-N-[3-(1H-imidazol-1-yl)propyl]benzeneacetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.54 g. of 4-fluorophenylacetic acid, 1.62 g. of 1,1'-carbonyldiimidazole and 30 ml. of tetrahydrofuran was stirred for 2 hours, then 1.98 g. of 1H-imidazole-1-propanamine dihydrochloride was added. Stirring was continued at room temperature for an additional 18 hours, then at reflux temperature for 5 hours, 5 ml. of water was added, the mixture was heated for 30 minutes and then concentrated to remove the volatile material. The residue was diluted with methylene chloride and 25 ml. of 1N sodium hydroxide and the layers separated. The organic layer was washed with water, dried over magnesium sulfate and concentrated, giving the desired product as a viscous oil.

Workup

  1. additionA mixture of 1.54 g
  2. temperatureat reflux temperature for 5 hours
  3. temperaturethe mixture was heated for 30 minutes
  4. concentrationconcentrated
  5. customto remove the volatile material
  6. additionThe residue was diluted with methylene chloride and 25 ml
  7. customof 1N sodium hydroxide and the layers separated
  8. washThe organic layer was washed with water
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-10943a0c07ab4282b49f50323488230c
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

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