HCID 20131146, compound → 1-[2-amino-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole
Reaction equation
[N:1]([CH:4]([CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:1][CH:4]([CH2:11][O:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-[2-azido-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole (5.1 g, 0.018M) in dry tetrahydrofuran (10 ml) was added dropwise to a stirred slurry of lithium aluminium hydride (0.68 g, 0.018M) in dry tetrahydrofuran (40 ml) at room temperature under a stream of dry nitrogen. When the addition was complete the reaction mixture was heated under reflux for 18 hours. The solvent was evaporated off under reduced pressure and the residue was extracted with ethyl acetate, washed with saturated aqueous ammonium chloride solution and dried (MgSO4). The solvent was evaporated off under reduced pressure to give 1-[2-amino-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole as an oil (3.6 g) which was used directly without further purification.
Workup
- additionWhen the addition
- temperaturewas heated
- temperatureunder reflux for 18 hours
- customThe solvent was evaporated off under reduced pressure
- extractionthe residue was extracted with ethyl acetate
- washwashed with saturated aqueous ammonium chloride solution
- dry with materialdried (MgSO4)
- customThe solvent was evaporated off under reduced pressure
Sources & evidence
- ORD record
- ord-b54f1dc69bc243d6a71cd29dc450acca
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04567189
Reaction notes
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