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Water → {3-[4-(2-Ethylbenzimidazol-1-yl)-piperidin-1-yl]-propyl}-(4-fluorophenyl)-amine

HRID 2240284
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HRID 2240284 반응식
[CH2:1]([C:3]1[N:7]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[N:4]=1)[CH3:2].Cl[CH2:19][CH2:20][CH2:21][NH:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:1]([C:3]1[N:7]([CH:8]2[CH2:9][CH2:10][N:11]([CH2:19][CH2:20][CH2:21][NH:22][C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[CH2:12][CH2:13]2)[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[N:4]=1)[CH3:2]
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참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12769738(3-Chloropropyl)-(4-fluorophenyl)amineHCID 575860322-ethyl-1-(piperidin-4-yl)-1H-1,3-benzodiazole

생성물 1

HCID 58599524{3-[4-(2-Ethylbenzimidazol-1-yl)-piperidin-1-yl]-propyl}-(4-fluorophenyl)-amine수율 37%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

To a stirred solution of 2-ethyl-1-piperidin-4-yl-1H-benzimidazole (0.6 g) and (3-chloropropyl)-(4-fluorophenyl)amine (0.4 g) in DMF (7 ml) was added K2CO3 (1.1 g) and KI (0.1 g). The mixture was heated at 100° C. for 2 h, and then allowed to cool to rt. Water (50 ml) was added and the mixture extracted with ethyl acetate (80 ml), and the organic layer separated and washed with water. This was further dried and concentrated in vacuo. The oil was purified by flash chromatography (95:5 DCM:MeOH), and the solid recrystallised from ether to yield 0.3 g of the title compound as colourless crystals. Mp. 121-124° C.

후처리

  1. temperatureto cool to rt
  2. extractionthe mixture extracted with ethyl acetate (80 ml)
  3. customthe organic layer separated
  4. washwashed with water
  5. customThis was further dried
  6. concentrationconcentrated in vacuo
  7. customThe oil was purified by flash chromatography (95:5 DCM:MeOH)
  8. customthe solid recrystallised from ether

출처 및 근거

ORD 기록
ord-508265322b7740cdbb5bf02580017fd6
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07723360B2

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