4-Pyridinecarboxaldehyde → N-(2,2-Diethoxyethyl)pyridine-4-methylamine

HRID 2361972Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][NH2:6])[CH3:2].[N:10]1[CH:15]=[CH:14][C:13]([CH:16]=O)=[CH:12][CH:11]=1>>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][NH:6][CH2:16][C:13]1[CH:14]=[CH:15][N:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

Reactant 2

HCID 133894-Pyridinecarboxaldehyde

HCID 695242,2-Diethoxyethylamine

Product 1

HCID 96638N-(2,2-Diethoxyethyl)pyridine-4-methylamineYield 44%

Procedure

According to the procedure described in the synthesis method of Compound IX-2, 2,2-diethoxyethanamine (162.8 ml, 1120 mmol) was reacted with 4-pyridinecarboxaldehyde (120 g, 1120 mmol) and the obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate and ethyl acetate:ethanol=15:1) to obtain the title compound (110 g, 44%).

Workup

customthe obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate and ethyl acetate:ethanol=15:1)

Sources & evidence

ORD record: ord-ec58fcb1e2af4b3c8e30f41355930003
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691819B2

Reaction notes

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