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

HRID 375530

반응식

HRID 375530 반응식
[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

참가 물질

7

반응물 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

생성물 2

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fa436fedf31d4580a07fc0fcbdf639d6
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05486517

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