3-Nitro-4-piperidin-1-ylpyridine → HCID 178419854, compound

HRID 1918912Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15]CCCC1)([O-])=O>P(OCC)(OCC)OCC>[N:10]1[C:9]23[CH2:8][CH2:7][NH:6][CH2:5][CH:4]2[NH:1][CH:8]=[CH:9][C:4]3=[N:1][CH:15]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A 500-mL single-neck round-bottomed flask equipped with a reflux condenser and magnetic stirrer was purged with nitrogen and charged with 159a (6.00 g, 29.0 mmol) and triethyl phosphite (200 mL). After heating at 110° C. for 24 h, the triethyl phosphite was removed under reduced pressure, and the residue was partitioned between methylene chloride (200 mL) and water (100 mL). The organic layer was separated, and the aqueous layer was extracted with methylene chloride (2×100 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 53% yield (2.66 g) of 159b as a yellow solid: mp 94-95° C.; 1H NMR (500 MHz, CDCl3) d 8.98 (s, 1H), 8.37 (d, 1H, J=6.0 Hz), 7.22 (d, 1H, J=6.0 Hz), 4.09 (t, 2H, J=6.0 Hz), 3.11 (t, 2H, J=6.0 Hz), 2.15 (m, 2H), 2.05 (m, 2H); MS (APCI+) m/z 174.1 (M+H).

Workup

customA 500-mL single-neck round-bottomed flask equipped with a reflux condenser and magnetic stirrer
customwas purged with nitrogen
customthe triethyl phosphite was removed under reduced pressure
customthe residue was partitioned between methylene chloride (200 mL) and water (100 mL)
customThe organic layer was separated
extractionthe aqueous layer was extracted with methylene chloride (2×100 mL)
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-702a29c2bc454b8aaca28de64615fba7
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618107B2

Reaction notes

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