2-Chloroimidazoline sulfate → 2-[4-(1-Isopropylaminocarbonylpiperidin-4-ylmethyl)-phenyl]amino-imidazoline

HRID 2121059Notes

Reaction equation

HRID 2121059 reaction equation
[CH:1]([NH:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].S(O)(O)(=O)=O.Cl[C:27]1[NH:28][CH2:29][CH2:30][N:31]=1>CC(O)C>[CH:1]([NH:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:27]3[NH:31][CH2:30][CH2:29][N:28]=3)=[CH:18][CH:19]=2)[CH2:11][CH2:12]1)=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 125033982-Chloroimidazoline sulfateHCID 218768574-(1-Isopropylaminocarbonylpiperidin-4-ylmethyl)-phenylamine

Product 1

HCID 218768082-[4-(1-Isopropylaminocarbonylpiperidin-4-ylmethyl)-phenyl]amino-imidazolineYield 59.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-(1-isopropylaminocarbonylpiperidin-4-ylmethyl)-phenylamine (0.64 g, 2.31 mmol) and 2-chloro-2-imidazoline sulfate (0.70 g, 3.47 mmol) in 2-propanol (20 mL) was heated under reflux for 30 minutes. The reaction mixture was concentrated in vacuo. The residue was diluted with water, basified with 10% sodium hydroxide solution and extracted into dichloromethane. The organic layer was washed with water and brine, dried (Na2SO4), and concentrated in vacuo. The crude product was chromatographed on neutral aluminum oxide, eluting with 5% methanol/dichloromethane, and crystallized from ethyl acetate containing some ethanol, to give 2-[4-(1-isopropylaminocarbonylpiperidin-4-ylmethyl)-phenyl]amino-imidazoline (0.47 g, 59%) as a white solid, m.p. 191-192° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted into dichloromethane
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude product was chromatographed on neutral aluminum oxide
  10. washeluting with 5% methanol/dichloromethane
  11. customcrystallized from ethyl acetate containing some ethanol

Sources & evidence

ORD record
ord-4513ffe0bf65476b9e9380f4feec032b
Source dataset
uspto-grants-2004_02
Patent number
US06693200B2

Reaction notes

Loading…