1-Isopropylpiperazine → (2-chloro-3-methyl-3H-imidazol-4-yl)-(4-isopropyl-piperazin-1-yl)-methanone

HRID 12448

Reaction equation

HRID 12448 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[C:5]([C:8]([OH:10])=O)=[CH:4][N:3]=1.[CH:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:13])[CH3:12].[Cl-].ClC1N(C)CC[NH+]1C>C1(C)C=CC=CC=1.CCN(C(C)C)C(C)C.CCOC(C)=O>[Cl:1][C:2]1[N:6]([CH3:7])[C:5]([C:8]([N:17]2[CH2:18][CH2:19][N:14]([CH:11]([CH3:13])[CH3:12])[CH2:15][CH2:16]2)=[O:10])=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 780131-IsopropylpiperazineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 534244292-Chloro-1-methyl-1H-imidazole-5-carboxylic acid

Product 1

HCID 59338485(2-chloro-3-methyl-3H-imidazol-4-yl)-(4-isopropyl-piperazin-1-yl)-methanone

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

Under nitrogen, 2-chloro-3-methyl-3H-imidazole-4-carboxylic acid (0.161 g, 1.0 mmol) is dissolved in toluene (5 mL, anhydrous) and DIEA (0.26 mL). N-isopropylpiperazine (0.2 M in toluene; 5.5 mL; 1.1 mmol) is added followed by the slow addition of 2-chloro-1,3-dimethylimidazolinium chloride (0.3 M in acetonitrile; 4.0 mL; 1.2 mmol). The reaction mixture is stirred at rt for 2 hr and is then diluted with EtOAc and washed with NaOH (1 N). The aqueous layer is drained and reextracted with EtOAc and the combined organic extracts are extracted twice with HCl (1 N). The combined acidic aqueous extracts are washed with EtOAc then basified with NaOH (2.5 M). The resulting basic aqueous solution is extracted three times with EtOAc and the combined organic extracts are washed with brine, then dried over Na2SO4, filtered and concentrated in vacuo.

Workup

  1. washwashed with NaOH (1 N)
  2. extractionthe combined organic extracts are extracted twice with HCl (1 N)
  3. washThe combined acidic aqueous extracts are washed with EtOAc
  4. extractionThe resulting basic aqueous solution is extracted three times with EtOAc
  5. washthe combined organic extracts are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c2f61fb48db41e3902576a0f542c4cc
Source dataset
uspto-grants-2010_06
Patent number
US07728009B1

Linked notes

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