Potassium Carbonate → 1-(2-(Piperidin-1-YL)ethyl)-1H-imidazol-2-amine

HRID 536137Notes

Reaction equation

HRID 536137 reaction equation
S(O)(O)(=O)=O.[NH2:6][C:7]1[NH:8][CH:9]=[CH:10][N:11]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C=O)C>[N:22]1([CH2:21][CH2:20][N:8]2[CH:9]=[CH:10][N:11]=[C:7]2[NH2:6])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 135136Bis(2-amino-1H-imidazole) sulphate

Product 1

HCID 534024741-(2-(Piperidin-1-YL)ethyl)-1H-imidazol-2-amineYield 22.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Aminoimidazole monosulfate (500 mg, 1.89 mmol) and potassium carbonate (580 mg, 4.16 mmol) were suspended in DMF (2 mL) and chloroethyl piperidine mono hydrochloride (766 mg, 4.16 mmol) was added. The reaction was heated at 100° C. for 2.5 hours before being cooled to room temperature and filtered. The filtrate was concentrated and purified by column chromatography (95:4.5:0.5 dichloromethane: methanol: aqueous ammonia) and the product was isolated as a brown oil (83 mg, 11%).

Workup

  1. temperaturebefore being cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography (95:4.5:0.5 dichloromethane: methanol: aqueous ammonia)

Sources & evidence

ORD record
ord-f6ed629322f448498436809f26ce79e7
Source dataset
uspto-grants-2014_10
Patent number
US08859563B2

Reaction notes

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