Phosgene → 5-Isocyanato-1,3-dioxaindane

HRID 5849

Reaction equation

HRID 5849 reaction equation
[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.[C:11](Cl)(Cl)=[O:12]>C1(C)C=CC=CC=1>[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([N:6]=[C:11]=[O:12])=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 843101,3-Benzodioxol-5-amine

Product 1

HCID 52232135-Isocyanato-1,3-dioxaindane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,4-methylenedioxyaniline (275 mg; 2.0 mmol) in toluene (15 ml) and phosgene (4.75 ml; 20% in toluene; 9 mmol) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 3,4-methylenedioxyphenylisocyanate. The crude product was added to 3-[4-(2-chlorophenyl) -1-piperazinyl]propanol (510 mg; 2.0 mmol) in toluene (30 ml) was refluxed for 16 h. The reaction mixture was then concentrated and submitted to flash chromatography on silica gel 60 eluting with toluene graduated to toluene/ethyl acetate (1:3). The product was taken up in ethanol which was treated with hydrogen chloride in ether. Recrystallization from methanol/ether afforded 550 mg of the title compound. M.p. 211°-213° C. MS (70 eV): m/z 37%, M+), 254 (28), 209 (100), 163 (75), 138 (32), 70 (42).

Workup

  1. temperaturewas refluxed for 6 h
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ec421ddd018040c2b602d046cea0785d
Source dataset
uspto-grants-1993_09
Patent number
US05246935

Linked notes

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