2-Chloroethyl isocyanate → (4,5-Dihydro-oxazol-2-yl)-[2-(4-fluoro-phenyl)-1-phenyl-ethyl]-amine

HRID 1441217Notes

Reaction equation

HRID 1441217 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH2:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.Cl[CH2:18][CH2:19][N:20]=[C:21]=[O:22]>C1COCC1>[O:22]1[CH2:18][CH2:19][N:20]=[C:21]1[NH:16][CH:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 150089772-(4-Fluorophenyl)-1-phenylethan-1-amine

Product 1

HCID 68699396(4,5-Dihydro-oxazol-2-yl)-[2-(4-fluoro-phenyl)-1-phenyl-ethyl]-amineYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-fluoro-phenyl)-1-phenyl-ethylamine (1.50 g) in THF was treated dropwise with 2-chloroethyl isocyanate (0.89 g) at 0° C. After stirring overnight at room temperature the solvent was evaporated and the residue dissolved in dimethoxy ethane (25 ml). DBU (1,8-diazabicyclo[5.4.0]undec-7-en) was added (1.78 g) and the reaction mixture heated under reflux for 1 hour. Column chromatography on silica yielded 1.3 g of the title compound.

Workup

  1. customwas evaporated
  2. dissolutionthe residue dissolved in dimethoxy ethane (25 ml)
  3. additionDBU (1,8-diazabicyclo[5.4.0]undec-7-en) was added (1.78 g)
  4. temperaturethe reaction mixture heated
  5. temperatureunder reflux for 1 hour

Sources & evidence

ORD record
ord-167148461f49402e8f84650cda7d4398
Source dataset
uspto-grants-2010_02
Patent number
US07655600B2

Reaction notes

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