Water → HCID 178444761, compound

HRID 2421276Notes

Reaction equation

HRID 2421276 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].O>CN(C)C=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 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 19349209HCID 19349209, compoundHCID 178420358HCID 178420358, compound

Product 1

HCID 178444761HCID 178444761, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-benzyl(4-[1,1′-biphenyl]-4-yl-1H-imidazol-2-yl)methanamine (1 g; 0.0024 mol; prepared under experimental conditions similar to those previously and using suitable starting reagents and reaction products) is diluted in 15 ml of dimethylformamide. Potassium carbonate (1 g; 0.0073 mol) is added at 23° C. then hexane bromide (0.34 ml; 0.0024 mol) is added fairly slowly. The reaction mixture is brought to about 70° C. for 3 hours before being poured into ice-cooled water. The mixture is extracted with ethyl acetate and the organic phase is 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/7-3), a light yellow-coloured solid is obtained in the form of a paste (yield of 13%). Free base. Melting point: 120-122° C.

Workup

  1. customprepared under experimental conditions similar to those previously and
  2. customreagents and reaction products)
  3. additionbefore being poured into ice-
  4. extractionThe mixture is extracted with ethyl acetate
  5. washthe organic phase is 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/7-3)
  10. customa light yellow-coloured solid is obtained in the form of a paste (yield of 13%)

Sources & evidence

ORD record
ord-8b0339aa35af48ea8153ebc65fdfc68b
Source dataset
uspto-grants-2011_06
Patent number
US07956075B2

Reaction notes

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