Water → HCID 178482717, compound

HRID 1591780Notes

Reaction equation

HRID 1591780 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]([CH2:12][NH:13][CH3:14])[NH:10][CH:11]=2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>CN(C)C=O>[CH2:27]([N:13]([CH3:14])[CH2:12][C:9]1[NH:10][CH:11]=[C:7]([C:4]2[CH:5]=[CH:6][C:1]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:2][CH:3]=2)[N:8]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178483028HCID 178483028, compound

Product 1

HCID 178482717HCID 178482717, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4-[1,1′-biphenyl]-4-yl-1H-imidazol-2-yl)-N-methylmethanamine (1 g; 0.003 mol; prepared under experimental conditions similar to those previously and using suitable starting reagents and reaction products) is diluted in 20 ml of dimethylformamide. Potassium carbonate (1.23 g; 0.009 mol) is added at 23° C. then benzyl bromide (0.34 ml; 0.003 mol) is added fairly slowly. The reaction mixture is stirred at this temperature for 48 hours then poured in ice-cooled water. The mixture is extracted with ethyl acetate and the organic phase washed with water. After drying over magnesium sulphate, the solvents are concentrated using a rotary evaporator. After purification on a silica column (eluent: ethyl acetate-heptane/8-2), a white-coloured solid is obtained in the form of a paste (yield of 16%). Free base. Melting point: 106-108° C.

Workup

  1. customprepared under experimental conditions similar to those previously and
  2. customreagents and reaction products)
  3. additionthen poured in ice-
  4. extractionThe mixture is extracted with ethyl acetate
  5. washthe organic phase washed with water
  6. dry with materialAfter drying over magnesium sulphate
  7. concentrationthe solvents are concentrated
  8. customa rotary evaporator
  9. customAfter purification on a silica column (eluent: ethyl acetate-heptane/8-2)
  10. customa white-coloured solid is obtained in the form of a paste (yield of 16%)

Sources & evidence

ORD record
ord-0e74487ebdf54cc2b0deba4b8be1035a
Source dataset
uspto-grants-2007_11
Patent number
US07291641B2

Reaction notes

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