Diphosgene → 1-(4-Isocyanatophenyl)piperidin-2-one

HRID 496039Notes

Reaction equation

HRID 496039 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=[O:22])=[CH:12][CH:11]=1>C1COCC1>[N:9]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=[O:22])=[CH:12][CH:11]=1)=[C:2]=[O:3]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 114581781-(4-Aminophenyl)piperidin-2-one

Product 1

HCID 111952821-(4-Isocyanatophenyl)piperidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.2 0.032 ml of trichloromethyl chloroformate is added under a nitrogen atmosphere to a solution of 50 mg of 1-(4-aminophenyl)piperidin-2-one (prepared from 1-(4-nitrophenyl)piperidin-2-one by hydrogenation using Raney nickel as catalyst) in 5 ml of THF, and the mixture is subsequently refluxed for 1.5 hours, giving 1-(4-isocyanatophenyl)piperidin-2-one (“AB”).

Workup

  1. temperaturethe mixture is subsequently refluxed for 1.5 hours

Sources & evidence

ORD record
ord-8cdb87b54c0b4dbcac7f853bfa815304
Source dataset
uspto-grants-2005_09
Patent number
US06943179B2

Reaction notes

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