Triethylamine → 3-(4-Trifluoromethylbenzoyl)piperidine-2,4-dione

HRID 1196414Notes

Reaction equation

HRID 1196414 reaction equation
C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=1.[NH:31]1[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][C:32]1=[O:38]>CN(C)C=O.ClCCl>[F:29][C:19]([F:18])([F:30])[C:20]1[CH:21]=[CH:22][C:23]([C:24]([CH:33]2[C:34](=[O:37])[CH2:35][CH2:36][NH:31][C:32]2=[O:38])=[O:26])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 99664-(Trifluoromethyl)benzoic acidHCID 76257Diethyl cyanophosphonateHCID 108878632,4-Piperidinedione

Product 1

HCID 198981603-(4-Trifluoromethylbenzoyl)piperidine-2,4-dioneYield 15.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Dry triethylamine (3.24 g) was added at 0°-5° C. to a stirred solution of diethyl cyanophosphate (1.96 g), 4-trifluoromethylbenzoic acid (2.28 g) and piperidine-2,4-dione (1.13 g) in dry dimethylformamide (50 ml) and the mixture stirred at ambient temperature for 5 hours. The mixture was diluted with dichloromethane (70 ml) and the solution washed successively with 2N hydrochloric acid (70 ml) and water (5×30 ml). The dichloromethane solution was dried over magnesium sulphate and evaporated under reduced pressure to give a brown solid which was recrystallised from toluene (11 ml) to give 3-(4-trifluoromethylbenzoyl)piperidine-2,4-dione (0.44 g), mp 197°-200° C., as a pale green crystalline solid.

Workup

  1. washthe solution washed successively with 2N hydrochloric acid (70 ml) and water (5×30 ml)
  2. dry with materialThe dichloromethane solution was dried over magnesium sulphate
  3. customevaporated under reduced pressure
  4. customto give a brown solid which
  5. customwas recrystallised from toluene (11 ml)

Sources & evidence

ORD record
ord-4b6e11fd396849cbb1636a910c7c00fa
Source dataset
uspto-grants-1992_05
Patent number
US05114461

Reaction notes

Loading…