Sodium Chloride → HCID 18988032, compound

HRID 2396149Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:19]I.[Cl-].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH3:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-[2-(N-t-butoxycarbonylamino)ethyl]-pyridine (1.8 g) in N,N-dimethylformamide (7 ml) was added dropwise to a suspension of sodium hydride (0.39 g) in N,N-dimethylformamide (7 ml) which was cooled at 0° C. The mixture was stirred at 0° C. for 1 hour. Methyl iodide (1.4 g) was added to this solution at the same temperature. After stirring at 0° C. for 1 hour and at ambient temperature for 2 hours, the mixture was poured into ice water, saturated with sodium chloride, and extracted with ethyl acetate 3 times. The combined organic layer was washed with saturated sodium thiosulfate, saturated sodium bicarbonate and saturated sodium chloride successively, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel chromatography (ethyl acetate:n-hexane, 3:1, V/V, as eluent) to give 2-[2-(N-t-butoxycarbonyl-N-methylamino)ethyl]-pyridine (1.47 g) as an oil.

Workup

stirringAfter stirring at 0° C. for 1 hour and at ambient temperature for 2 hours
extractionextracted with ethyl acetate 3 times
washThe combined organic layer was washed with saturated sodium thiosulfate, saturated sodium bicarbonate and saturated sodium chloride successively
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified with silica gel chromatography (ethyl acetate:n-hexane, 3:1, V/V, as eluent)

Sources & evidence

ORD record: ord-28459f0e9bde4a6fa0552dfc1c51ed2d
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05491132

Reaction notes

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