Acetic Acid → 3-[3-(Dimethylamino)propyl]-3-(3-methoxyphenyl)-4,4-dimethyl-2,6-piperidinedione

HRID 1658325Notes

Reaction equation

HRID 1658325 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])(C#N)[C:10]([CH3:23])([CH3:22])[CH:11]=[C:12]([O:19]CC)[N:13]2CCOCC2)[CH:6]=[CH:7][CH:8]=1.S(=O)(=O)(O)O.N.[C:38](O)(=[O:40])C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[C:10]([CH3:23])([CH3:22])[CH2:11][C:12](=[O:19])[NH:13][C:38]2=[O:40])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 1118Sulfuric AcidHCID 54495153HCID 54495153, compound

Product 1

HCID 409143-[3-(Dimethylamino)propyl]-3-(3-methoxyphenyl)-4,4-dimethyl-2,6-piperidinedione

Procedure

The but-1-ene product above is dissolved in acetic acid (45 ml) and sulphuric acid (30 ml) added. The resultant mixture is maintained at 100° until cyclisation is complete, as determined by working-up an aliquot and studying the infra-red spectrum of the product. The solution is cooled and poured into excess ammonia/ice, the pH adjusted to about 8 with aqueous ammonia and the solution extracted with chloroform (three times). The organic solutions are combined, dried, filtered and the solvent removed. The residual dione is crystallised and recrystallised from ethanol to give white crystals of 3-(m-methoxyphenyl)-3-(γ-N,N-dimethylaminopropyl)-4,4-dimethyl-2,6-dioxo-piperidine, m.pt. 167°-9°.

Workup

  1. temperatureThe solution is cooled
  2. extractionthe solution extracted with chloroform (three times)
  3. customdried
  4. filtrationfiltered
  5. customthe solvent removed
  6. customThe residual dione is crystallised
  7. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-26611a979bba41738d2e98165f528871
Source dataset
uspto-grants-1976_06
Patent number
US03963729

Reaction notes

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