Ammonia → Tert-butyl 4-(5-cyano-3-methylpyridin-2-yl)piperazine-1-carboxylate

HRID 2411234Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17](Br)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.N.[CH3:24][N:25](C)C=O>[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([C:24]#[N:25])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

Under a nitrogen stream, 4-(5-bromo-3-methylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (3.13 g) was dissolved in N,N-dimethylformamide (30 mL), zinc cyanide (1.03 g) and tetrakistriphenylphosphine palladium(0) (0.51 g) were added, and the mixture was stirred at 120° C. for 4 hr. After completion of the reaction, to the reaction mixture was added water/saturated aqueous ammonium chloride solution/28% aqueous ammonia (4:4:1), and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (2.46 g).

Workup

customAfter completion of the reaction
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
customthe solvent was evaporated
customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record: ord-9ef1defde2454c238f75db14c9933266
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08816079B2

Reaction notes

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