Sodium borohydride → 2-((2,4-Dichlorobenzyl)(methyl)amino)-1-phenylethanol
Reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]([CH3:15])[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]([CH3:15])[CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Into a 250 ml 3-necked roundbottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-((2,4-dichlorobenzyl)(methyl)amino)-1-phenylethanone (4.3 g, 14.01 mmol, 1.00 equiv) in methanol (50 mL). This was followed by the addition of NaBH4 (1.5 g, 39.47 mmol, 2.82 equiv) in several batches at 0° C. The resulting solution was stirred for 30 min at 0° C. in a water/ice bath. The reaction was then quenched by the addition of 20 mL of acetone. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:80-1:20). This resulted in 3.4 g (79%) of the title compound as a white solid.
Workup
- customInto a 250 ml 3-necked roundbottom flask purged
- temperaturemaintained with an inert atmosphere of nitrogen
- customThe reaction was then quenched by the addition of 20 mL of acetone
- concentrationThe resulting mixture was concentrated under vacuum
Sources & evidence
- ORD record
- ord-e0c6fab508634aa68debc573a7ce18fa
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541448B2
Reaction notes
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