Imidazole → UK 34787

HRID 1856007Notes

Reaction equation

HRID 1856007 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[CH:14]([CH3:16])[CH3:15])[CH3:3].[NH:17]1C=CN=[CH:18]1>C1(C)C(C)=CC=CC=1>[N:2]1([CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:14]([CH3:16])[CH3:15])[CH:1]=[CH:18][N:17]=[CH:3]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 23347374HCID 23347374, compound

Product 1

HCID 194468UK 34787Yield 26.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3-(Dimethylaminomethyl)-2-isopropylindole (1.7 g.) and imidazole (0.6 g.) were heated at the reflux temperature in xylene (50 ml.) for a period of one hour. The solution was then cooled to room temperature (~20° C.) and petroleum ether (b.p. 60°-80° C.) was added until a faint cloudiness appeared. The resulting mixture was then allowed to stand at room temperature (~20° C.), whereupon the desired product soon crystallized from solution and was subsequently recovered by means of suction filtration. Recrystallization of the latter material from industrial methylated spirits (i.e., ethyl alcohol denatured with methanol) then gave pure 3-(imidazol-1-ylmethyl)-2-isopropylindole (yield, 0.5 g.), m.p. 241°-216° C.

Workup

  1. additionwas added until a faint cloudiness
  2. customto stand at room temperature
  3. custom(~20° C.)
  4. customwhereupon the desired product soon crystallized from solution
  5. filtrationwas subsequently recovered by means of suction filtration
  6. customRecrystallization of the latter material from industrial methylated spirits (i.e., ethyl alcohol denatured with methanol)

Sources & evidence

ORD record
ord-130b5ad27782424cba5ecad3f3060411
Source dataset
uspto-grants-1980_08
Patent number
US04217357

Reaction notes

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