Phenethylamine → 3-fluoro-N-(2-phenylethyl)benzamide

174.9 ml (1.39 mol) of phenylethylamine were dissolved in 600 ml of dichloromethane and admixed with 196.0 ml (1.41 mol, 1.01 eq.) of triethylamine. Subsequently, 221.0 g (1.39 mmol) of 3-fluorobenzoyl chloride were added dropwise to the solution at 0° C. such that the temperature did not rise above 40° C. The mixture was stirred at RT for 18 h and the precipitated solid was dissolved in 1000 ml of dichloromethane. The mixture was washed four times with 200 ml of dilute NaOH, 1N HCl and saturated NaHCO3 solution. The organic phase was removed, dried over MgSO4 and concentrated under reduced pressure. The solid was filtered off with suction and washed twice with a little dichloromethane. 289.52 g of a white solid were obtained with >99% purity (by HPLC), corresponding to 85.4% of theory.

1. customdid not rise above 40° C
2. washThe mixture was washed four times with 200 ml of dilute NaOH, 1N HCl and saturated NaHCO3 solution
3. customThe organic phase was removed
4. dry with materialdried over MgSO4
5. concentrationconcentrated under reduced pressure
6. filtrationThe solid was filtered off with suction
7. washwashed twice with a little dichloromethane

ORD record

ord-25cc840fdd8f49ecb11b45a68512064d

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846920B2