Hydrochloric Acid → HCID 21498322, compound

HRID 1730501Notes

Reaction equation

HRID 1730501 reaction equation
[OH:1][C:2]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)([CH3:10])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].[ClH:19].OC(C1C=CN=CC=1)(C)CC1C=CC=CC=1.Cl>[Pd].O.C(O)(=O)C>[ClH:19].[OH:1][C:2]([CH:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1)([CH3:10])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 21498325HCID 21498325, compoundHCID 21498326HCID 21498326, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21498322HCID 21498322, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The mixture of 4.0 g of 4-(α-hydroxy-α-methylphenethyl)-pyridine, 100 ml of glacial acetic acid, 20 ml of water and 2.0 g of 10% palladium on charcoal is treated with hydrogen at 4.1 atm and room temperature. Following the theoretical uptake of hydrogen the reaction mixture is filtered to remove the catalyst. The filtrate is evaporated to dryness under reduced pressureand the residue treated with 50% aqueous sodium hydroxide. The resulting mixture is extracted with methylene chloride; the extract is dried and evaporated under reduced pressure to give an oil which is converted into the hydrochloride with ethanolic hydrogen chloride to give 4-(α-hydroxy-α-methylphenethyl)-piperidine hydrochloride of melting point 162°-164°.

Workup

  1. filtrationis filtered
  2. customto remove the catalyst
  3. customThe filtrate is evaporated to dryness
  4. additiontreated with 50% aqueous sodium hydroxide
  5. extractionThe resulting mixture is extracted with methylene chloride
  6. customthe extract is dried
  7. customevaporated under reduced pressure
  8. customto give an oil which

Sources & evidence

ORD record
ord-a8422b72924249bb8711111ca8b01d63
Source dataset
uspto-grants-1976_11
Patent number
US03992546

Reaction notes

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