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

HRID 2121062Notes

Reaction equation

HRID 2121062 reaction equation
[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(O)(O)(=O)=O.Cl[C:30]1[NH:31][CH2:32][CH2:33][N:34]=1>CC(O)C>[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:30]4[NH:34][CH2:33][CH2:32][N:31]=4)=[CH:21][CH:22]=3)[CH2:12][CH2:11]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 125033982-Chloroimidazoline sulfateHCID 218770334-(1-Benzenesulfonylpiperidin-4-ylmethyl)-phenylamine

Product 1

HCID 120943962-[4-(1-Benzenesulfonylpiperidin-4-ylmethyl)-phenyl]amino-imidazolineYield 89%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-(1-benzenesulfonylpiperidin-4-ylmethyl)-phenylamine (0.28 g, 0.83 mmol) and 2-chloro-2-imidazoline sulfate (0.25 g, 1.25 mmol) in 2-propanol (20 mL) was heated under reflux for 30 minutes under nitrogen atmosphere. The reaction mixture was concentrated in vacuo. The residue was basified with 10% sodium hydroxide solution and extracted with dichloromethane. The organic layer was washed with cold water and brine, dried, and solvents removed in vacuo. The residue was chromatographed on neutral aluminum oxide, eluting with 1% methanovdichloromethane, to give 2-[4-(1-benzenesulfonylpiperidin-4-ylmethyl)-phenyl]amino-imidazoline (0.29 g, 89%) as a foam. Analysis for C21H26N4O2S.5H2O: Calc.: C, 61.89; H, 6.68; N, 13.75; Found: C, 62.00; H, 6.52; N, 13.85.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes under nitrogen atmosphere
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with cold water and brine
  6. customdried
  7. customsolvents removed in vacuo
  8. customThe residue was chromatographed on neutral aluminum oxide
  9. washeluting with 1% methanovdichloromethane

Sources & evidence

ORD record
ord-b2f329af4890436ca935711ff6dd705c
Source dataset
uspto-grants-2004_02
Patent number
US06693200B2

Reaction notes

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