Triethylamine → 4-(1H-Benzimidazol-2-yl)-N-[2-(4-phenyl-1-piperazinyl)ethyl]benzamide

HRID 375530Notes

Reaction equation

HRID 375530 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1.[C:19]1([N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][NH2:33])[CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>ClCCl>[NH3:1].[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:33][CH2:32][CH2:31][N:28]2[CH2:29][CH2:30][N:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26][CH2:27]2)=[O:16])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 7594194-(1h-Benzimidazol-2-yl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 47425032-(4-Phenylpiperazin-1-yl)ethan-1-amine

Product 2

HCID 222AmmoniaHCID 189930524-(1H-Benzimidazol-2-yl)-N-[2-(4-phenyl-1-piperazinyl)ethyl]benzamideYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(1H-benzimidazol-2-yl)benzoic acid (Example E) (0.50 g), 2-(4-phenylpiperazin-1-yl)ethylamine (0.77 g), 1-(3-dimethylaminopropyl)3-ethylcarbodiimide hydrochloride (0.44 g) and triethylamine (0.29 mL) in dichloromethane (20 mL) is stirred at room temperature for 2 days. The mixture is washed with water (50 mL), dried over MgSO4, filtered and evaporated. The residue is purified by MPLC on silica gel eluting with 100:8:1 dichloromethane: ethanol:0.880 aqueous ammonia to give 0.33 g of the title compound as a beige solid; mp 190°-192° C.

Workup

  1. washThe mixture is washed with water (50 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by MPLC on silica gel eluting with 100:8:1 dichloromethane

Sources & evidence

ORD record
ord-fa436fedf31d4580a07fc0fcbdf639d6
Source dataset
uspto-grants-1996_01
Patent number
US05486517

Reaction notes

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