Acetone Cyanohydrin → HCID 14800187, compound

HRID 1196409Notes

Reaction equation

HRID 1196409 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[NH:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][C:15]1=[O:21].C(N(CC)CC)C.CC(C)(O)C#N>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([CH:16]2[C:17](=[O:20])[CH2:18][CH2:19][NH:14][C:15]2=[O:21])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 108677844-Chloro-2-nitrobenzoyl chlorideHCID 108878632,4-Piperidinedione

Product 1

HCID 14800187HCID 14800187, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-chloro-2-nitrobenzoyl chloride (5.8 g) in dry dichloromethane (10 ml) was added over 5 minutes to a stirred solution of piperidine-2,4-dione (3.0 g) and triethylamine (5.5 ml) in dry dichloromethane (100 ml) and the mixture was stirred at ambient temperature for 3 hours. Acetone cyanohydrin (0.5 ml) was added and the mixture was stirred at ambient temperature for 18 hours. The solution was washed successively with 2N hydrochloric acid (50 ml) and water (2×100 ml), dried over sodium sulphate and evaporated under reduced pressure to give a solid residue which was recrystallised from ethyl acetate (70 ml) to give 3-(4-chloro-2-nitrobenzoyl)piperidine-2,4-dione (1.6 g), mp 161°-164° C., as a light brown crystalline solid.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 18 hours
  2. washThe solution was washed successively with 2N hydrochloric acid (50 ml) and water (2×100 ml)
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customto give a solid residue which
  6. customwas recrystallised from ethyl acetate (70 ml)

Sources & evidence

ORD record
ord-cf6458ad81174137aef3d2fbdddd3ea0
Source dataset
uspto-grants-1992_05
Patent number
US05114461

Reaction notes

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