Hydrochloric Acid → HCID 12952294, compound

HRID 1284459Notes

Reaction equation

HRID 1284459 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9](=[O:12])[CH2:10][CH3:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[ClH:13].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[CH2:20]=O.Cl>C(OCC)(=O)C>[ClH:13].[CH3:11][CH:10]([CH2:20][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:9]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1)=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 2723721Piperidine, hydrochloride (1:1)HCID 38535211-(3,4-dimethylphenyl)propan-1-one

Product 1

HCID 12952294HCID 12952294, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

72.0 g of 3',4'-dimethylpropiophenone, 59.4 g of piperidine hydrochloride and 20.0 g of paraformaldehyde, 300 ml of ethyl acetate and 1 ml of concentrated hydrochloric acid were heated with stirring under reflux for 2.5 hours, while distilling off water generated through the reaction. After cooling, crystals precipitated were filtered and recrystallized from a mixture of alcohol-acetone, yielding white crystals of the object product. Each filtrate was collected, concentrated under reduced pressure to dryness, and dissolved in water. The solution was washed with ether, then adjusted to be alkaline with 5N sodium hydroxide and extracted with ether. The extract was washed and then ether was removed after addition of concentrated hydrochloric acid, and the residue was recrystallized from a mixture of alcohol-acetone, yielding white crystals of 2,3',4'-trimethyl-3-piperidinopropiophenone hydrochloride (total yield 61.3%), m.p. 184°-185° C.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. distillationwhile distilling off water
  3. customgenerated through the reaction
  4. temperatureAfter cooling
  5. customcrystals precipitated
  6. filtrationwere filtered
  7. customrecrystallized from a mixture of alcohol-acetone
  8. customyielding white crystals of the object product
  9. customEach filtrate was collected
  10. concentrationconcentrated under reduced pressure to dryness
  11. dissolutiondissolved in water
  12. washThe solution was washed with ether
  13. extractionextracted with ether
  14. washThe extract was washed
  15. customether was removed
  16. additionafter addition of concentrated hydrochloric acid
  17. customthe residue was recrystallized from a mixture of alcohol-acetone

Sources & evidence

ORD record
ord-3aa9649797a946bf951f57e613ba1c30
Source dataset
uspto-grants-1986_01
Patent number
US04563454

Reaction notes

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