Water → 2-(4-(5-Trifluoromethyl-2-pyridinyloxy)phenyl)ethylamine

HRID 491267Notes

Reaction equation

[H-].[Na+].[NH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.Cl[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=1.O>CN(C=O)C>[F:21][C:20]([F:23])([F:22])[C:17]1[CH:18]=[CH:19][C:14]([O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][NH2:3])=[CH:7][CH:8]=2)=[N:15][CH:16]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium hydride/60 percent oil dispersion (0.72 mg, 18 mmol) was added in portions to a slurry of tyramine (2.1 g, 15 mmol) in anh. DMF (25 mL). After 15 minutes, 2-chloro-5-(trifluoromethyl)pyridine (2.9 g, 16 mmol) was added neat and the reaction heated to 50° C. for 3 hours. After cooling, the reaction was poured into water (100 mL) and extracted with ethyl acetate (3×50 mL). The organic portions were combined and washed with brine (50 mL) and dried (Na2SO4). Filtration and removal of solvent left a brown residue that partially solidified. This was triturated in minimal ethyl acetate and collected by filtration, leaving product as a white solid, 3.0 g, 10.6 mmol, 71 percent yield.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate (3×50 mL)
washwashed with brine (50 mL)
dry with materialdried (Na2SO4)
filtrationFiltration and removal of solvent
waitleft a brown residue that
customThis was triturated in minimal ethyl acetate
filtrationcollected by filtration
customleaving product as a white solid, 3.0 g, 10.6 mmol, 71 percent yield

Sources & evidence

ORD record: ord-70ec13d2b36d4e6fbf58a42c9d793ab5
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531482B2

Reaction notes

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