3-Phenylpropyl isocyanate → N-(3-phenylpropyl)-N'-[(2,2-dimethoxy-2-(4-pyridyl)-1-(4-fluorophenyl)ethyl)] urea
Reaction equation
[CH3:1][O:2][C:3]([O:19][CH3:20])([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[NH2:5].[N:21]([CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[C:22]=[O:23]>C1COCC1>[C:27]1([CH2:26][CH2:25][CH2:24][NH:21][C:22]([NH:5][CH:4]([C:6]2[CH:7]=[CH:8][C:9]([F:12])=[CH:10][CH:11]=2)[C:3]([O:2][CH3:1])([O:19][CH3:20])[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[O:23])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1Participants
4
Procedure
To a solution of 2,2-dimethoxy-2-(4-pyridyl)-1-(4-fluorophenyl)ethanamine (1.22 g, 4.4 mmol) in THF (10 mL) was added a solution of (3-isocyanatopropyl)-benzene (1.61 g, 10 mmol) in THF (10 mL). The resulting mixture was stirred at room temperature for 30 minutes. The reaction was quenched by addition of water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined ethyl acetate extract was washed with water (50 mL), brine (50 mL) and dried with Na2SO4. After removal of solvent, the crude product was purified by column chromatography to yield the product as a light brown solid.
Workup
- customThe reaction was quenched by addition of water (50 mL)
- extractionextracted with ethyl acetate (2×50 mL)
- extractionThe combined ethyl acetate extract
- washwas washed with water (50 mL), brine (50 mL)
- dry with materialdried with Na2SO4
- customAfter removal of solvent
- customthe crude product was purified by column chromatography
Sources & evidence
- ORD record
- ord-7af0c282d60b4223892d0a22325ba8af
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07132544B2
Reaction notes
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