3-(pyridin-4-yl)benzaldehyde → N-methyl(3-(pyridin-4-yl)phenyl)methanamine

HRID 2205294Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH:10]=O)=[CH:3][CH:2]=1.[BH3-][C:16]#[N:17].[Na+].CN.Cl>CO>[CH3:16][NH:17][CH2:10][C:9]1[CH:12]=[CH:13][CH:14]=[C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Into a 250 mL round-bottom flask was placed a solution of 3-(pyridin-4-yl)benzaldehyde (10 g, 54.6 mmol, 1 equiv) in MeOH (200 mL), NaBH3CN (10.33 g, 164 mmol, 3 equiv) and CH3NH2.HCl (18.44 g, 273 mmol, 5 equiv). The mixture was stirred overnight at 60° C. The solvents were removed under reduced pressure. The residue was added to 100 mL of H2O and extracted with 5×200 mL of ethyl acetate. After removal of solvent, the crude product was purified by re-crystallization from ethyl acetate to give 5 g of N-methyl-(3-(pyridin-4-yl)phenyl)methylamine as a white solid.

Workup

customInto a 250 mL round-bottom flask was placed
customThe solvents were removed under reduced pressure
additionThe residue was added to 100 mL of H2O
extractionextracted with 5×200 mL of ethyl acetate
customAfter removal of solvent
customthe crude product was purified by re-crystallization from ethyl acetate

Sources & evidence

ORD record: ord-d9132b967ec54bbc96cc2062698b7224
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371285B2

Reaction notes

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