Triethylamine → HCID 19898290, compound

HRID 1196413Notes

Reaction equation

HRID 1196413 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][C:9]1=[O:15].[C:16](C#N)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl.[Cl-].[Zn+2].[Cl-]>[C:16]([CH:10]1[C:11](=[O:14])[CH2:12][CH2:13][NH:8][C:9]1=[O:15])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11953PhenylglyoxylonitrileHCID 108878632,4-Piperidinedione

Product 1

HCID 19898290HCID 19898290, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Dry triethylamine (1.33 g) was added at 0°-5° C. to a stirred suspension of piperidine-2,4-dione (1.13 g), anhydrous zinc chloride (1.64 g) and benzoyl cyanide (1.31 g) in dry dichloromethane (50 ml) and the mixture stirred at ambient temperature for 18 hours. The mixture was washed successively with 2N hydrochloric acid (2×30 ml) and water (3×30 ml) dried over magnesium sulphate and evaporated under reduced pressure to give a pale yellow solid which was recrystallised from acetonitrile (0.5 ml) to give 3-benzoylpiperidine-2,4-dione (0.5 g), mp 164°-165° C., as a cream crystalline solid.

Workup

  1. washThe mixture was washed successively with 2N hydrochloric acid (2×30 ml) and water (3×30 ml)
  2. dry with materialdried over magnesium sulphate
  3. customevaporated under reduced pressure
  4. customto give a pale yellow solid which
  5. customwas recrystallised from acetonitrile (0.5 ml)

Sources & evidence

ORD record
ord-f731e76dfcb24bfe8f10f51dc97e141c
Source dataset
uspto-grants-1992_05
Patent number
US05114461

Reaction notes

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