Potassium Carbonate → 6-chloro-3-nitro-N-(3-piperidin-1-ylpropyl)pyridin-2-amine

HRID 1727035Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[N:7]1([CH2:13][CH2:14][CH2:15][NH2:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[C:20]([Cl:27])[N:19]=1>C1(C)C=CC=CC=1>[Cl:27][C:20]1[N:19]=[C:18]([NH:16][CH2:15][CH2:14][CH2:13][N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 20 °C

Procedure

Potassium carbonate (540 mg, 1.5 eq) and 3-piperidino-propylamine (420 mg, 1 eq) are added successively to 2,6-dichloro-3-nitropyridine (500 mg, 1 eq) in solution in toluene (10 ml). After stirring for 2 hours at a temperature of approximately 20° C., the mixture is concentrated under reduced pressure at 40° C. then water (20 ml) and dichloromethane (70 ml) are added. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the solid obtained, by flash chromatography on silica gel (eluent: heptane/ethyl acetate 3:7 to 100% ethyl acetate), produces the expected compound in the form of a yellow solid (473 mg; 61% yield).

Workup

concentrationthe mixture is concentrated under reduced pressure at 40° C.
additionwater (20 ml) and dichloromethane (70 ml) are added
extractionAfter decantation and extractions
washthe combined organic phases are washed with salt water
dry with materialdried over Na2SO4
concentrationthen concentrated under reduced pressure at 40° C
customPurification of the solid
customobtained, by flash chromatography on silica gel (eluent: heptane/ethyl acetate 3:7 to 100% ethyl acetate)

Sources & evidence

ORD record: ord-72809767555d4c14904f18cf70924148
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495009B2

Reaction notes

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