Hydrochloric Acid → HCID 51063713, compound

HRID 922377Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].Cl>O.CC#N>[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([C:2]2[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of 6-bromopicolinaldehyde (1.50 g, 8.10 mmol), 1-methylpiperazine (2, 4.04 g, 40.0 mmol), potassium carbonate (4.46 g, 32.0 mmol) and anhydrous CH3CN (10 mL) was placed in a sealed vessel and the mixture was heated at 110° C. for 17 h. The mixture was diluted with water (50 mL) and brought to pH 7 using 2 N aq. HCl (15 mL). The resulting solution was extracted with CH2Cl2 (3×50 mL) and the combined extracts were washed with brine (200 mL). The solution was dried (Na2SO4), filtered, concentrated and purified by silica gel chromatography eluting with 0-5% CH3OH in CH2Cl2 to afford the title compound (0.528 g, 32%) as an orange oil: 1H NMR (500 MHz, CDCl3) δ 9.84 (s, 1H), 7.62 (t, J=8.0 Hz, 1H), 7.27 (d, J=7.0 Hz, 1H), 6.85 (d, J=7.0 Hz, 1H), 3.67-3.65 (m, 4H), 2.55-2.52 (m, 4H), 2.36 (s, 3H).

Workup

customwas placed in a sealed vessel
extractionThe resulting solution was extracted with CH2Cl2 (3×50 mL)
washthe combined extracts were washed with brine (200 mL)
dry with materialThe solution was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
custompurified by silica gel chromatography
washeluting with 0-5% CH3OH in CH2Cl2

Sources & evidence

ORD record: ord-a92046446d8140ed9d693b5799da469a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278940B2

Reaction notes

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