Allylamine → N-2-Propen-1-yl-6-[4-(trifluoromethyl)phenyl]-2-pyridinamine

HRID 1269670Notes

Reaction equation

[CH2:1]([NH2:4])[CH:2]=[CH2:3].Br[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[N:7]=1>C(O)C.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:1]([NH:4][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][CH:13]=2)[N:7]=1)[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of of allylamine (0.447 mL, 5.96 mmol) and 2-bromo-6-[4-(trifluoromethyl)phenyl]pyridine (0.1 g, 0.298 mmol) in ethanol (5 mL) were heated at 100° C. in a 25 mL pressure vessel. After heating overnight the reaction was cooled and copper sulfate was added and heating continued at 100° C. overnight. After this time the reaction was allowed to coole to room temperature and concentrated in vacuo. Purification by SPE (Silica, 10 g) eluting 3:1 cyclohexane:chloroform afforded the title compound as a dark yellow solid (0.062 g).

Workup

temperatureAfter heating overnight the reaction
temperaturewas cooled
temperatureheating
customto coole to room temperature
concentrationconcentrated in vacuo
customPurification by SPE (Silica, 10 g)
washeluting 3:1 cyclohexane

Sources & evidence

ORD record: ord-546d2e7ec73a4f6e9519db19b5087601
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199239B2

Reaction notes

Loading…