Potassium Carbonate → HCID 178444761, compound

HRID 230389Notes

Reaction equation

HRID 230389 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[NH:11][CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br-].[CH3:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>CN(C)C=O.O>[CH2:1]([N:8]([CH2:9][C:10]1[NH:11][CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:19][CH:20]=2)[N:14]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 19349209HCID 19349209, compoundHCID 178420358HCID 178420358, compound

Product 1

HCID 178444761HCID 178444761, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-benzyl(4-(1,1′-biphenyl)-4-yl-1H-imidazol-2-yl)methanamine (1 g; 0.0024 mol; prepared according to experimental conditions analogous to the preceding examples and using the appropriate starting compounds and reaction products) was diluted in 15 ml dimethylformamide. Potassium carbonate (1 g; 0.0073 mol) was added at about 23° C. and then hexane bromide (0.34 ml; 0.0024 mol) was added quite slowly. The reaction mixture was brought around the temperature of about 70° C. for about 3 hours before being poured in icy water. The mixture was extracted with ethyl acetate and the organic phase washed with water. After drying over magnesium sulfate, the solvents were concentrated using a rotative evaporator. After purification over a silica column (eluent: ethyl acetate-heptane/7-3), a light yellow solid was obtained in the form of a glue (yield of 13%). Free base. Melting point: 120-122° C. MH+=424.3.

Workup

  1. customprepared
  2. customcompounds and reaction products)
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic phase washed with water
  5. dry with materialAfter drying over magnesium sulfate
  6. concentrationthe solvents were concentrated
  7. customa rotative evaporator
  8. customAfter purification over a silica column (eluent: ethyl acetate-heptane/7-3)
  9. customa light yellow solid was obtained in the form of a glue (yield of 13%)

Sources & evidence

ORD record
ord-f275cb5a30914e55be346624a8f8f52f
Source dataset
uspto-grants-2009_07
Patent number
US07566734B2

Reaction notes

Loading…