Potassium Carbonate → 2-[4-(4-Methoxy-phenyl)-piperazin-1-ylmethyl]-1H-benzoimidazole

HRID 481957

반응식

HRID 481957 반응식
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][C:9]1[NH:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1>CN(C=O)C.O>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[CH2:31][CH2:30][N:29]([CH2:8][C:9]3[NH:10][C:11]4[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=4[N:13]=3)[CH2:28][CH2:27]2)=[CH:24][CH:25]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 785712-ChloromethylbenzimidazoleHCID 2697221-(4-Methoxyphenyl)piperazine

생성물 1

HCID 6676752-[4-(4-Methoxy-phenyl)-piperazin-1-ylmethyl]-1H-benzoimidazole

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Potassium carbonate (2.76 g, 20 mmol) and 2-(chloromethyl)benzimidazole (1.70 g, 10 mmol) were added to a solution of 1-(4-methoxyphenyl)piperazine (1.92 g, 10 mmol) in DMF (20 ml) under a nitrogen atmosphere and the mixture was stirred overnight. The mixture was diluted with water (200 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with water (100 ml) and brine (100 ml), dried (MgSO4) and evaporated in vacuo to give a solid which was recrystallised from toluene to give the title compound as a buff solid (731 mg, 23%). mp 214°-216° C.; (Found: C, 70.80; H, 6.82; N, 17.28. C19H22N4O requires C, 70.78; H, 6.88; N, 17.38%); δH (DMSO-d6) 2.59-2.62 (4H, m, 2×piperazinyl CH2), 3.03-3.05 (4H, m, 2×piperazinyl CH2), 3.67 (3H, s, OCH3), 3.77 (2H, s, CH2N), 6.79-6.82 (2H, m, ArH), 6.85-6.89 (2H, m, ArH), 7.10-7.17 (2H, m, ArH), 7.43 (1H, d, J 6.9 Hz, ArH), 7.55 (1H, d, J 6.9 Hz, ArH), and 12.30 (1H, brs, NH); m/z (CI+, NH3) 323 (M+1)+.

후처리

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washThe combined organic layers were washed with water (100 ml) and brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customto give a solid which
  6. customwas recrystallised from toluene

출처 및 근거

ORD 기록
ord-7a4c52c842dd453c923e51dcabcd707f
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05792768

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