Ammonium Hydroxide → 4-(2,6-Dichlorophenyl)-2,6-piperidinedione

HRID 1241877Notes

Reaction equation

HRID 1241877 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([CH2:14][C:15]([OH:17])=O)[CH2:10][C:11](O)=[O:12].[NH4+:18].[OH-]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[CH2:14][C:15](=[O:17])[NH:18][C:11](=[O:12])[CH2:10]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 21936962HCID 21936962, compound

Product 1

HCID 219369454-(2,6-Dichlorophenyl)-2,6-piperidinedione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
190 °C

Procedure

14.5 g (52 mmol) of 3-(2,6-dichloro-phenyl)-pentanedioic acid were dissolved in 140 mL of conc. NH4OH solution. All the volatiles were removed in vacuo and the resulting solid was heated to 190° C. for 6 h. The crude reaction mixture was taken up in CH2Cl2, the organic phase was washed with 0.1 M Na2CO3 solution, dried and evaporated to dryness. The resulting crude solid was triturate with Et2O, filtered and dried, yielding 9.37 g of the title compound.

Workup

  1. customAll the volatiles were removed in vacuo
  2. customThe crude reaction mixture
  3. washthe organic phase was washed with 0.1 M Na2CO3 solution
  4. customdried
  5. customevaporated to dryness
  6. customThe resulting crude solid was triturate with Et2O
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-c3d646f2c211477e94a8215d637c44a6
Source dataset
uspto-grants-2006_10
Patent number
US07115633B2

Reaction notes

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