Water → (2-Aminomethyl-4-trifluoromethyl-phenyl)-cyclopropylmethyl-propyl-amine
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:10][N:11]([CH2:25][CH2:26][CH3:27])[C:12]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:13]=2[CH:14]=[N:15]O)[CH2:9][CH2:8]1.O.[OH-].[Na+]>O1CCCC1>[NH2:15][CH2:14][C:13]1[CH:17]=[C:18]([C:21]([F:23])([F:24])[F:22])[CH:19]=[CH:20][C:12]=1[N:11]([CH2:10][CH:7]1[CH2:9][CH2:8]1)[CH2:25][CH2:26][CH3:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Lithium aluminum hydride (1.4 g) is suspended in tetrahydrofuran (50 ml) and thereto is added dropwise a 2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzaldehyde oxime (5.7 g) in tetrahydrofuran (20 ml) under ice-cooling, and the mixture is stirred at room temperature overnight. To the reaction solution are added water (1.4 ml), a 2N-aqueous sodium hydroxide solution (2.8 ml) and water (2.8 ml) successively under ice-cooling, and the insoluble material is removed by filtration and the filtrate is concentrated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (chloroform:ethyl acetate=10:1) to give (2-aminomethyl-4-trifluoromethyl-phenyl)-cyclopropylmethyl-propyl-amine as a crude product (5.1 g).
Workup
- temperaturecooling
- customthe insoluble material is removed by filtration
- concentrationthe filtrate is concentrated under reduced pressure
- customThe resulting residue is purified by NH-silica gel column chromatography (chloroform:ethyl acetate=10:1)
Sources & evidence
- ORD record
- ord-4e33afa813bf404bba56c4b12bc2ec30
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906517B2
Reaction notes
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