Imidazole → 6-(1H-imidazol-1-ylmethyl)quinoline dihydrochloride

HRID 2081610Notes

Reaction equation

HRID 2081610 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[ClH:1].[ClH:1].[N:13]1([CH2:2][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[N:9]=[CH:8][CH:7]=[CH:6]3)[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 146661986-(Chloromethyl)quinoline

Product 1

HCID 199671056-(1H-imidazol-1-ylmethyl)quinoline dihydrochlorideYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 12.3 parts of 6-(chloromethyl)quinoline, 9.5 parts of 1H-imidazole, 19.2 parts of potassium carbonate and 135 parts of N,N-dimethylformamide was stirred for 3 hours at 80° C. After evaporation to dry, the residue was taken up in water and further purified according to similar procedures as described in example 12, yielding 10 parts (48%) of 6-(1H-imidazol-1-ylmethyl)quinoline dihydrochloride; mp. 254.6° C. (compound 19).

Workup

  1. customAfter evaporation
  2. customto dry
  3. customfurther purified

Sources & evidence

ORD record
ord-08373da993484e0094fc2413aa6efcf8
Source dataset
uspto-grants-1993_02
Patent number
US05185346

Reaction notes

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