Sodium borohydride → 2-((2,4-Dichlorobenzyl)(methyl)amino)-1-phenylethanol

HRID 1470095Notes

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

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-ff8d538c78b34524a12e4adf44d14280
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006281B2

Reaction notes

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