2-Chloroimidazoline sulfate → 2-[4-(4-Isopropoxymethyl-benzyl)-phenyl]-imidazoline
Reaction equation
[CH:1]([O:4][CH2:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14](N)=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)([CH3:3])[CH3:2].S(O)(O)(=O)=O.Cl[C:26]1[NH:27][CH2:28][CH2:29][N:30]=1>C(O)(C)C>[CH:1]([O:4][CH2:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:26]3[NH:30][CH2:29][CH2:28][N:27]=3)=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 4-(4-isopropoxymethylbenzyl)-phenylamine (400 mg, 1.57 mmol) in isopropanol (4.8 mL) at 20° C. under argon atmosphere was added 2-chloro-2-imidazoline sulfate (382 mg, 1.88 mmol). The mixture was heated to 80° C. and stirred for 3 hours. The solvent was evaporated in vacuo, and water and 10% sodium hydroxide was added to pH 11-12. The basic aqueous phase was extracted with dichloromethane (3x 20 mL), and the combined organic layers were washed with water, dried (Na2SO4), and evaporated in vacuo. The crude product was purified by flash chromatography, washed with 0.07M potassium carbonate, and concentrated to give pure 2-[4-(4-isopropoxymethyl-benzyl)-phenyl]-imidazoline (463 mg, 91%) as a clear oil.
Workup
- customThe solvent was evaporated in vacuo, and water and 10% sodium hydroxide
- additionwas added to pH 11-12
- extractionThe basic aqueous phase was extracted with dichloromethane (3x 20 mL)
- washthe combined organic layers were washed with water
- dry with materialdried (Na2SO4)
- customevaporated in vacuo
- customThe crude product was purified by flash chromatography
- washwashed with 0.07M potassium carbonate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8b19a98a856c46679d05d8cc0ce8aeb3
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06184242B2
Reaction notes
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