Benzoic Acid → HCID 18357059, compound

HRID 427469Notes

Reaction equation

HRID 427469 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NCC[C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)=[CH:15][CH:14]=1.[CH3:31][N:32](C)C=O>>[N:28]1[CH:29]=[CH:30][C:25]([N:22]2[CH2:21][CH2:20][N:19]([C:16]3[CH:15]=[CH:14][CH:13]=[C:18]([C:1](=[O:9])[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:17]=3[CH2:31][NH2:32])[CH2:24][CH2:23]2)=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 243Benzoic AcidHCID 6228Dimethylformamide3×HCID 18357083HCID 18357083, compound

Product 1

HCID 18357059HCID 18357059, compound

Procedure

To a solution of benzoic acid (22 mg) in dimethylformamide (2 ml), was added 1,1-carbonyldiimidazole (188 mg) in dimethylformamide (2 ml) and the solution stirred at ambient temperature for 1 hour. A solution of 1-[4-(2-aminoethyl)phenyl]-4-(4-pyridyl)piperazine (268 mg) in dimethylformamide (4 ml) was then added in one portion and the resulting solution stirred at ambient temperature for twelve hours. The solution was evaporated to dryness and aqueous sodium bicarbonate (8 ml, 1M) added. The mixture was d stirred vigorously at ambient temperature for thirty minutes. The solid was collected by filtration, washed with water to give 1-(4-pyridyl)-4-(benzoyl-aminomethyl-phenyl)piperazine (389 mg), retention time 11.49 mins (same HPLC conditions as in Example 57).

Workup

  1. stirringthe resulting solution stirred at ambient temperature for twelve hours
  2. customThe solution was evaporated to dryness and aqueous sodium bicarbonate (8 ml, 1M)
  3. additionadded
  4. stirringThe mixture was d stirred vigorously at ambient temperature for thirty minutes
  5. filtrationThe solid was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-44beb63a9b6447f3bb93e1e5e8a15948
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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