2-Pyridinemethanamine → N-(2,2-diethoxyethyl)pyridine-2-methylamine

Reaction equation

Br[CH2:2][CH:3]([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][NH2:17]>>[CH2:5]([O:4][CH:3]([O:7][CH2:8][CH3:9])[CH2:2][NH:17][CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=1)[CH3:6]

Participants

Reactant 2

HCID 195092-Pyridinemethanamine

HCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 81407N-(2,2-diethoxyethyl)pyridine-2-methylamineYield 65.9%

Procedure

According to the procedure described in the synthesis method of Compound IX-1, 2-bromo-1,1-diethoxyethane (34.6 ml, 230 mmol) was reacted with 2-picolylamine (50 g, 460 mmol) and the obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate:ethanol=10:1) to obtain the title compound (34.0 g, 65%)

Workup

customthe obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate:ethanol=10:1)

Sources & evidence

ORD record: ord-dd86ad9eb50e4b2cac1cc1860c87a625
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126981B2

Reaction notes

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