Benzenepentanoic acid → HCID 178520571, compound

HRID 726221Notes

Reaction equation

HRID 726221 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:14]1[CH:18]=[C:17]([CH2:19][NH2:20])[N:16]=[CH:15]1.[Cl-].[Cl-].[Ca+2]>C1COCC1>[NH:14]1[CH:18]=[C:17]([CH2:19][NH:20][C:11](=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:16]=[CH:15]1

Participants

5

Reactant 3

HCID 16757Benzenepentanoic acidHCID 5284359Calcium ChlorideHCID 178510438HCID 178510438, compound

Product 1

HCID 178520571HCID 178520571, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8 mmol of N,N'-carbonyldiimidazole and 8 mmol of 5-phenylpentanoic acid are introduced successively into 10 ml of absolute THF and, after having stirred for 30 min, 8 mmol of (1H-imidazol-4-yl)methanamine are added to the mixture, moisture being excluded using CaCl2. At the end of 14 h, the solvent is removed by distilling under vacuum. The remaining oil is mixed with a small amount of water. The title compound is filtered under vacuum, dried and crystallized from ethanol/diethyl ether.

Workup

  1. customAt the end of 14 h, the solvent is removed
  2. distillationby distilling under vacuum
  3. additionThe remaining oil is mixed with a small amount of water
  4. filtrationThe title compound is filtered under vacuum
  5. customdried
  6. customcrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-d0da577244674241a0611497968cfd17
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Reaction notes

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