Methyl iodide → N-(3-Aminopropyl)-N-methylpyridin-2-amine

HRID 464333Notes

Reaction equation

[H-].[Na+].[NH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[H][H].I[CH3:17]>CS(C)=O.O>[NH2:3][CH2:4][CH2:5][CH2:6][N:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:17]

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of sodium hydride (0.82 g) in DMSO (20 ml) was added 2-(3-aminopropylamino)pyridine (4.7 g). The mixture was stirred and slowly heated under nitrogen to 85° C. After the evolution of hydrogen had ceased the mixture was cooled to room temperature and iodomethane (4.41 g) in DMSO (5 ml) added keeping the temperature below 35° C. After stirring for a further 30 minutes water (200 ml) was added and the resulting mixture extracted with chloroform. The extract was washed with water followed by 2N hydrochloric acid. The pH of the acid washings was raised to 14 (NaOH) and extracted again with chloroform. This final extract was dried (K2CO3) and stripped to an oil 3.84 g. Chromatography (silica gel, 10% ammoniacal methanol/dichloromethane) afforded 2-[N-(3-aminopropyl)-N-methylamino]pyridine 2.0 g (39%) as an oil.

Workup

temperaturewas cooled to room temperature
customthe temperature below 35° C
additionwas added
extractionthe resulting mixture extracted with chloroform
washThe extract was washed with water
temperatureThe pH of the acid washings was raised to 14 (NaOH)
extractionextracted again with chloroform
extractionThis final extract
dry with materialwas dried (K2CO3)

Sources & evidence

ORD record: ord-45e3c7011e574197a11ed4ca4a3d2289
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04547506

Reaction notes

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