Dimethylamine → 3-(N,N-Dimethylamino)methylpyridine-2-carbonitrile

HRID 254156Notes

Reaction equation

Br[CH2:2][C:3]1[C:4]([C:9]#[N:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[CH3:11][NH:12][CH3:13].C(=O)([O-])[O-]>CC#N>[CH3:11][N:12]([CH2:2][C:3]1[C:4]([C:9]#[N:10])=[N:5][CH:6]=[CH:7][CH:8]=1)[CH3:13]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 3-bromomethylpyridine-2-carbonitrile (591 mg, 3.0 mmol) in MeCN (10 mL) was treated with dimethylamine (7.9-M in water, 1.9 mL, 15 mmol) and heated at 50° C. for 4 h. The solution was treated with MP-carbonate (2.0 g, 6.0 mmol), stirred for 30 min, filtered through Celite and the residue was washed with EtOAc. The filtrate was concentrated in vacuo, and the crude product was purified by chromatography [SiO2; MeOH:EtOAc:isohexane (0:4:1-1:9:0)] to give the title compound (541 mg, 96%) as an orange oil; NMR δH (400 MHz, CDCl3) 2.31 (6H, s), 3.67 (2H, s), 7.50 (1H, dd, J 8.0, 4.5 Hz), 7.94 (1H, dd, J 8.0, 1.5 Hz) and 8.61 (1H, dd, J 4.5, 1.5 Hz); M/Z 162 (M+H)+.

Workup

filtrationfiltered through Celite
washthe residue was washed with EtOAc
concentrationThe filtrate was concentrated in vacuo
customthe crude product was purified by chromatography [SiO2; MeOH:EtOAc:isohexane (0:4:1-1:9:0)]

Sources & evidence

ORD record: ord-ce6e176d568342f5b8e5de626ae73384
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875600B2

Reaction notes

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