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

HRID 2240284
Notes
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Reaction equation

HRID 2240284 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-508265322b7740cdbb5bf02580017fd6
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07723360B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes