Acetone Cyanohydrin → 3-(4-Chloro-2-nitrobenzoyl)-6,6-dimethylpiperidine-2,4-dione
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.[CH3:14][C:15]1([CH3:23])[NH:20][C:19](=[O:21])[CH2:18][C:17](=[O:22])[CH2:16]1.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:18]2[C:17](=[O:22])[CH2:16][C:15]([CH3:23])([CH3:14])[NH:20][C:19]2=[O:21])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-chloro-2-nitrobenzoyl chloride (4.4 g) in dry dichloromethane (5 ml) was added at 5°-10° C. to a stirred solution of 6,6-dimethylpiperidine-2,4-dione (2.8 g) and triethylamine (2.8 ml) in dry dichloromethane (50 ml) and the mixture was stirred at ambient temperature for 18 hours. Triethylamine (8.4 ml) and acetone cyanohydrin (0.4 ml) were added successively to the solution and the mixture was stirred at ambient temperature for 4 hours. The resulting solution was washed successively with 2N hydrochloric acid (25 ml) and water (3×25 ml), dried over sodium sulphate and evaporated under reduced pressure to give a yellow solid which was recrystallised from acetonitrile to give 3-(4-chloro-2-nitrobenzoyl)-6,6-dimethylpiperidine-2,4-dione (4 g), mp 162°-162.5° C., as a yellow crystalline solid.
Workup
- stirringthe mixture was stirred at ambient temperature for 4 hours
- washThe resulting solution was washed successively with 2N hydrochloric acid (25 ml) and water (3×25 ml)
- dry with materialdried over sodium sulphate
- customevaporated under reduced pressure
- customto give a yellow solid which
- customwas recrystallised from acetonitrile
Sources & evidence
- ORD record
- ord-cce4e7944be34b27b9fe87c1ed71c64c
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05114461
Reaction notes
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