Water → HCID 68448925, compound

HRID 1516760Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([C:11]([CH3:24])([CH3:23])[C:12]([N:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[N:25]1([CH2:31][CH2:32][CH2:33][NH2:34])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[CH2:15]([N:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:12](=[O:13])[C:11]([CH3:24])([C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([NH:34][CH2:33][CH2:32][CH2:31][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:3]=1)[CH3:23])[CH:16]([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(3-chloro-4-nitrophenyl)-N,N-diisobutyl-2-methylpropanamide (2.39 g), 3-piperidino-propylamine (1.9 g, 2 eq) and potassium carbonate (1.8 g, 2 eq) in DMF (40 ml) is heated at 100° C. for 24 hours then cooled down to ambient temperature. Water and ethyl acetate are added to the medium. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 and concentrated under reduced pressure. Purification of the residue obtained by flash chromatography on silica gel (eluent: dichloromethane 100% to dichloromethane/methanol 6:4) produces the expected compound in the form of a yellow oil (1.6 g, 51% yield).

Workup

temperaturethen cooled down to ambient temperature
extractionAfter decantation and extractions
washthe combined organic phases are washed with salt water
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customPurification of the residue
customobtained by flash chromatography on silica gel (eluent: dichloromethane 100% to dichloromethane/methanol 6:4)

Sources & evidence

ORD record: ord-0bfde3ca69c54f82a1634165e5df682a
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227485B2

Reaction notes

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