Diallylamine → HCID 67457450, compound

HRID 639696Notes

Reaction equation

[CH2:1]([NH:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11](Cl)[C:10]=1[N+:18]([O-:20])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH2:30]([NH:33][CH2:34][CH:35]=[CH2:36])[CH:31]=[CH2:32]>C(OC(O)C)C>[CH2:30]([N:33]([CH2:34][CH:35]=[CH2:36])[C:11]1[C:10]([N+:18]([O-:20])=[O:19])=[C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=1)[CH:31]=[CH2:32]

Participants

Conditions

Temperature: 100 °C

Procedure

Benzyl-(2-chloro-5,6-dimethyl-3-nitro-pyridin-4-yl)-amine (1.2 g, 4.1 mmol) was dissolved in ethoxyethanol (60 mL) and diisopropylethylamine (1.1 mL, 6.2 mmol) and diallylamine (0.76 mL, 6.2 mmol) added in one portion. The reaction mixture was heated in a sealed vessel at 100° C. overnight, and then concentrated in vacuo to an orange residue. This residue was purified directly by column chromatography on silica gel, using a gradient of 8:1→1:1 pentane:EtOAc as eluant to provide the title compound as a bright orange oil (938 mg, 65%).

Workup

concentrationconcentrated in vacuo to an orange residue
customThis residue was purified directly by column chromatography on silica gel

Sources & evidence

ORD record: ord-536e810ef9524d8daf770222d8953d0a
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691877B2

Reaction notes

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