p-Fluorophenethylamine → N-Benzyloxycarbonyl-2-(parafluorophenyl)ethylamine

HRID 1653687Notes

Reaction equation

HRID 1653687 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][NH2:21])=[CH:15][CH:14]=1>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:21][CH2:20][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4653p-FluorophenethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 23366829N-Benzyloxycarbonyl-2-(parafluorophenyl)ethylamineYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzylchloroformate (12.2 g, 72 mmol) was added dropwise to a stirred solution, at 0° C., of 4-fluorophenylethyl amine (9.42 g, 72 mmol) in 50 mL of DMF. The mixture was stirred for an additional 3 hours at the same temperature. The reaction was quenched with water and extracted with 3×100 mL of ethyl acetate. The combined ethyl acetate extracts were washed with 2×100 mL of 5% HCl, water and dried over Na2SO4. Evaporation of the solvent resulted in a yellowish solid which was purified by recrystallization from ethyl acetate-hexane to furnish 8.6 g (46% yield) of N-Benzyloxycarbonyl-2-(parafluorophenyl)ethylamine. mp 51°-52° C.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with 3×100 mL of ethyl acetate
  3. washThe combined ethyl acetate extracts were washed with 2×100 mL of 5% HCl, water
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the solvent
  6. customresulted in a yellowish solid which
  7. customwas purified by recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-646579b9a7824a2288ef11792a605fbf
Source dataset
uspto-grants-1995_04
Patent number
US05403851

Reaction notes

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