Triethylamine → N,N-Diethyl-N-{[3-(trifluoromethyl)phenyl]methyl}ethanaminium chloride

HRID 256106Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][Cl:7].[CH2:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14]>C(#N)C.C(OCC)C>[Cl-:7].[CH2:13]([N+:15]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:12])([F:11])[F:1])[CH:4]=1)[CH3:14]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 15.3 grams (0.08 mole) of 3-(trifluoromethyl)benzyl chloride and 8.0 grams (0.086 mole) of triethylamine in 50 milliliters of acetonitrile was heated 6 hours at 85° C. The mixture was then stirred over a weekend at room temperature. The crystals which formed were slurried in ethyl ether. The crude product was recovered by filtration and extracted with 600 milliliters of hot methyl ethyl ketone and 0.50 ml of methylene dichloride. The triethyl-(3-trifluoromethyl)benzyl) ammonium chloride was recoved by filtration in a yield of 13.7 grams. The product melted at 213°-215° C. The structure of the compound was confirmed by NMR.

Workup

customThe crystals which formed
filtrationThe crude product was recovered by filtration
extractionextracted with 600 milliliters of hot methyl ethyl ketone and 0.50 ml of methylene dichloride
filtrationThe triethyl-(3-trifluoromethyl)benzyl) ammonium chloride was recoved by filtration in a yield of 13.7 grams

Sources & evidence

ORD record: ord-aac5cef9dc2b4b7da5062e3bf09bef96
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04701211

Reaction notes

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