3,4-Dimethylaniline → (3,4-Dimethyl-phenyl)-[2-(5-trifluoromethyl-pyridin-2-yl)-ethyl]-amine

HRID 1094365Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[CH2:10])=[N:7][CH:8]=1.[CH3:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[CH3:21])[NH2:17].O.[OH-].[Cs+]>CN1C(=O)CCC1.C(OCC)(=O)C>[CH3:13][C:14]1[CH:15]=[C:16]([NH:17][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:11])[F:12])=[CH:8][N:7]=2)[CH:18]=[CH:19][C:20]=1[CH3:21]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 200 mg (0.92 mmol) 5-trifluoromethyl-2-vinyl-pyridine (CAS: 204569-89-1), 570 mg (4.62 mmol) 3,4-dimethylaniline and 33 mg (0.18 mmol) cesium hydroxide monohydrate in 2 mL NMP was heated in a 120° C. oil-bath for 22 hours. The mixture was cooled to room temperature and diluted with ethyl acetate. The solution was washed 3 times with water, dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 0.17 g (63%) of the title compound as a light yellow oil. MS (m/e): 295.2 [M+H]+.

Workup

temperatureThe mixture was cooled to room temperature
washThe solution was washed 3 times with water
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude oil was purified with flash column chromatography on silica eluting with a gradient
customformed from heptane and ethylacetate

Sources & evidence

ORD record: ord-1d95e61e8cd442bf865708c72aa6f22c
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133909B2

Reaction notes

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