Hydrochloric Acid → HCID 18377387, compound

HRID 372808Notes

Reaction equation

HRID 372808 reaction equation
[N:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)([O-])[O-].[K+].[K+]>CCOCC>[CH:7]1([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 12713183HCID 12713183, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18377387HCID 18377387, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

An ether solution of 48 g. of 1-piperidino-3,4-dihydronaphthalene as prepared above is treated with gaseous HCl to precipitate the salt. Rapid filtering to avoid hydrolysis by moisture followed by drying over potassium hydroxide in a vacuum dessicator provides a white powder salt which is added portionwise to an ether suspension of excess lithium aluminum hydride. After 1 hour of stirring, the excess reagent is decomposed by the cautious dropwise addition of potassium carbonate solution until a granular white precipitate forms. Filtration and concentration leaves an oil which is fractionally distilled to yield 25 g. of 1-(1-tetrahydronaphthyl)piperidine collected at 102°-106° (0.3 mm.).

Workup

  1. customto precipitate the salt
  2. filtrationRapid filtering
  3. customhydrolysis by moisture
  4. dry with materialby drying over potassium hydroxide in a vacuum dessicator
  5. customprovides a white powder salt which
  6. filtrationFiltration and concentration
  7. customleaves an oil which
  8. distillationis fractionally distilled
  9. customto yield 25 g
  10. customof 1-(1-tetrahydronaphthyl)piperidine collected at 102°-106° (0.3 mm.)

Sources & evidence

ORD record
ord-baa842e0ecf74a1d99588950e0d048cd
Source dataset
uspto-grants-1978_05
Patent number
US04092318

Reaction notes

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