4-Fluorophenyl isocyanate → N-(1-acetylpiperidin-4-yl)-N'-(4-fluorophenyl)urea

HRID 49783

Reaction equation

HRID 49783 reaction equation
Cl.[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH2:11])[CH2:7][CH2:6]1)(=[O:4])[CH3:3].[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=[O:21])=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C>ClCCl>[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:20]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)=[O:21])[CH2:7][CH2:6]1)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 709554-Fluorophenyl isocyanateHCID 81531DiisopropylethylamineHCID 172216421-Acetyl-4-aminopiperidine hydrochloride

Product 1

HCID 9860476N-(1-acetylpiperidin-4-yl)-N'-(4-fluorophenyl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 1-acetyl-4-aminopiperidine hydrochloride (536 mg) in dichloromethane (5 ml) were added 4-fluorophenyl isocyanate (375 μl) and diisopropylethylamine (575 μl ) at ambient temperature. After stirring for 3 hours, the reaction mixture was diluted with dichloromethane. An organic phase was separated and an aqueous phase was extracted with dichloromethane. A combined organic phase was dried over magnesium sulfate and the solvents were removed under reduced pressure. After crystallization from diisopropyl ether and n-hexane, N-(1-acetylpiperidin-4-yl)-N′-(4-fluorophenyl)urea (448 mg) was obtained.

Workup

  1. customAn organic phase was separated
  2. extractionan aqueous phase was extracted with dichloromethane
  3. dry with materialA combined organic phase was dried over magnesium sulfate
  4. customthe solvents were removed under reduced pressure
  5. customAfter crystallization from diisopropyl ether and n-hexane

Sources & evidence

ORD record
ord-791c61bd4d46488d9cd3f88bc69b7774
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Linked notes

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