Potassium Carbonate → 4,5-dichloro-2-methyl-1-(4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-imidazole

HRID 483872

Reaction equation

HRID 483872 reaction equation
[Br-].[N:2]1[CH:7]=[CH:6][CH:5]=[N:4][C:3]=1[N:8]1[CH2:17][CH2:16][N+:11]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:10][CH2:9]1.[Cl:18][C:19]1[N:20]=[C:21]([CH3:25])[NH:22][C:23]=1[Cl:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:18][C:19]1[N:20]=[C:21]([CH3:25])[N:22]([CH2:12][CH2:13][CH2:14][CH2:15][N:11]2[CH2:10][CH2:9][N:8]([C:3]3[N:2]=[CH:7][CH:6]=[CH:5][N:4]=3)[CH2:17][CH2:16]2)[C:23]=1[Cl:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3123904,5-Dichloro-2-methyl-1H-imidazoleHCID 6575058-Aza-5-azoniaspiro(4.5)decane, 8-(2-pyrimidinyl)-, bromide (1:1)

Product 1

HCID 99292344,5-dichloro-2-methyl-1-(4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 450 g (1.5 moles) of 8-(2-pyrimidinyl)-8-aza-5-azoniaspiro[4,5]decane bromide, 225 g (1.5 moles) of 4.5-dichloro-2-methylimidazole and 300 g (2.25 moles) of potassium carbonate in 2 l of dimethylformamide is heated to 130°-135° for 14 hours. The mixture is evaporated under vacuum, chloroform is added, the solution is washed with water, dried over sodium sulfate and evaporated under vacuum, and 503 g (91%) of 4,5-dichloro-2-methyl-1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-imidazole are obtained in liquid form.

Workup

  1. temperatureis heated to 130°-135° for 14 hours
  2. customThe mixture is evaporated under vacuum, chloroform
  3. additionis added
  4. washthe solution is washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under vacuum, and 503 g (91%) of 4,5-dichloro-2-methyl-1-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-1H-imidazole
  7. customare obtained in liquid form

Sources & evidence

ORD record
ord-a16ab31c82c946d3aceec834d8713024
Source dataset
uspto-grants-1993_07
Patent number
US05227486

Linked notes

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