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

HRID 222633

Reaction equation

HRID 222633 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-5a74d01fdcd14d459f877a5ccbc1b94d
Source dataset
uspto-grants-2012_06
Patent number
US08207334B2

Linked notes

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