Ethylamine → [3,6-Dimethyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-4-yl]-ethylamine

HRID 1831637Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[C:3]=1[CH3:19].[CH2:20]([NH2:22])[CH3:21]>CN1CCCC1=O.O>[CH3:19][C:3]1[C:4]([O:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])=[N:5][C:6]([CH3:8])=[CH:7][C:2]=1[NH:22][CH2:20][CH3:21]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-chloro-3,6-dimethyl-2-(2,4,6-trimethylphenoxy)-pyridine (1.330 g, 4.822 mmol) and 20 ml of ethyl amine in 13 ml of 1-methyl-2-pyrrolidinone was heated at 150° C. at 250 psi overnight in a pressure reactor. The reaction was heated an additional 24 hours at 175° C. and 300 psi. The reaction mixture cooled to room temperature and diluted with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give a brown oil. The oil residue was purified through silica gel column chromatography using chloroform to 2% methanol in chloroform as eluent to give 0.820 g (60%) of the title compound as a white solid, mp 115–116° C.

Workup

temperatureThe reaction was heated an additional 24 hours at 175° C.
temperatureThe reaction mixture cooled to room temperature
extractionextracted with ethyl acetate
customThe organic layer was dried
concentrationconcentrated
customto give a brown oil
customThe oil residue was purified through silica gel column chromatography

Sources & evidence

ORD record: ord-020a64af585d4854910b114b5d202b6b
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067664B1

Reaction notes

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