Pyridine → 2,2,2-trifluoro-N-[2-(4-methoxyphenyl)ethyl]acetamide

HRID 993151Notes

Reaction equation

HRID 993151 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](O)=[O:4].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH2:18])=[CH:12][CH:11]=1.N1C=CC=CC=1>C1COCC1>[F:1][C:2]([F:7])([F:6])[C:3]([NH:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[CH:11][CH:12]=1)=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 4657O-MethyltyramineHCID 6422Trifluoroacetic acid

Product 1

HCID 8856202,2,2-trifluoro-N-[2-(4-methoxyphenyl)ethyl]acetamideYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

32.2 ml (0.23 mol) of trifluoroacetic acid were added dropwise to a solution of 22.3 ml (0.15 mol) of 2-(4-methoxyphenyl)ethylamine and 24.7 ml (0.23 mol) of pyridine in 125 ml of absolute THF cooled to 5° C., and the resulting solution was stirred at RT for 3 h. The reaction solution was then poured onto 750 ml of ice, and the deposited precipitate was filtered off with suction and dried at 40° C. in a high vacuum. 36.3 g of the title compound were obtained as a beige solid.

Workup

  1. filtrationthe deposited precipitate was filtered off with suction
  2. customdried at 40° C. in a high vacuum

Sources & evidence

ORD record
ord-f7fdb8c8e9cf4d4096d09445ca6594aa
Source dataset
uspto-grants-2002_10
Patent number
US06472413B2

Reaction notes

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