Hydrochloric Acid → HCID 12952294, compound

HRID 1277383Notes

Reaction equation

HRID 1277383 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 froma 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 5 N sodium hydroxide and extracted with ether. The extract was washed and then ether was removed after addition ofconcentrated 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
  8. additionfroma mixture of alcohol-acetone
  9. customyielding white crystals of the object product
  10. customEach filtrate was collected
  11. concentrationconcentrated under reduced pressure to dryness
  12. dissolutiondissolved in water
  13. washThe solution was washed with ether
  14. extractionextracted with ether
  15. washThe extract was washed
  16. customether was removed
  17. additionafter addition ofconcentrated hydrochloric acid
  18. customthe residue was recrystallized from a mixture of alcohol-acetone

Sources & evidence

ORD record
ord-1bd3891de76b47cd9118e23283c56097
Source dataset
uspto-grants-1981_07
Patent number
US04277474

Reaction notes

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