Benzonitrile, p-imidazol-1-yl- → 4-(Imidazol-1-yl)benzylamine
Reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1>C1COCC1>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][NH2:11])=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=[CH:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4-(1-imidazolyl)-benzonitrile (1 g, 5.92 mmol) was dissolved in anhydrous THF (10 mL) and added drop-wise to a stirring solution of LAH-THF (1 M in THF, 18 mL) at room temperature. The reaction mixture was refluxed under Ar for 2 h and the progress was monitored by TLC. The mixture was cooled to 0° C. and quenched by drop-wise addition of a saturated Na2SO4—H2O solution. The mixture was stirred for 1 h and filtered to remove lithium salts. The filtrate was dried over anhydrous MgSO4 and concentrated to obtain 4-(1-imidazolyl)-benzylamine (0.8 g, 80%). LCMS: MH+=174.
Workup
- temperatureThe reaction mixture was refluxed under Ar for 2 h
- customquenched by drop-wise addition of a saturated Na2SO4—H2O solution
- filtrationfiltered
- customto remove lithium salts
- dry with materialThe filtrate was dried over anhydrous MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-90913a0c1e7f4e798730b84d9dd01ad7
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07119200B2
Reaction notes
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