(1R)-(+)-1-(4-Fluorophenyl)ethylamine → (R)-1-(1-(4-fluorophenyl)ethyl)urea

HRID 590774Notes

Reaction equation

HRID 590774 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[O-:11][C:12]#[N:13].[K+]>Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:12]([NH2:13])=[O:11])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6950187(1R)-(+)-1-(4-Fluorophenyl)ethylamineHCID 11378442Potassium cyanate

Product 1

HCID 117601722(R)-1-(1-(4-fluorophenyl)ethyl)urea

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

(R)-1-(4-Fluorophenyl)ethanamine (5.15 g, 37.0 mmol) was taken up in HCl (2N, 40 mL) and potassium cyanate (15.01 g, 185 mmol) was added. The mixture was stirred at 80° C. for 3 h. Upon cooling to room temperature, a precipitate formed which was collected by filtration and washed with water. The solid was partitioned between water and EtOAc, and the aqueous phase extracted once more with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give (R)-1-(1-(4-fluorophenyl)ethyl)urea. MS ESI calc'd. for C9H11FN2O [M+1]+ 183. found 183.

Workup

  1. temperatureUpon cooling to room temperature
  2. customa precipitate formed which
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customThe solid was partitioned between water and EtOAc
  6. extractionthe aqueous phase extracted once more with EtOAc
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d36bd88c69534b799ea41fc4267c8c23
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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