Hydrochloric Acid → 4-(3-Methylphenyl)piperidine--hydrogen chloride (1/1)

HRID 2071555Notes

Reaction equation

HRID 2071555 reaction equation
O(C([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)[CH2:12][CH2:11]1)=O)C1C=CC=CC=1.[OH-].[K+].O.[ClH:26]>C(O)C.CCOCC>[ClH:26].[C:18]1([CH3:22])[CH:19]=[CH:20][CH:21]=[C:16]([CH:13]2[CH2:12][CH2:11][NH:10][CH2:15][CH2:14]2)[CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 203117071-Phenoxycarbonyl-4-(3-toluyl)piperidine

Product 1

HCID 219369674-(3-Methylphenyl)piperidine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 11.9 g of 1-phenoxycarbonyl-4-(3-toluyl)piperidine and 75 ml of an aqueous 50% potassium hydroxide solution in 300 ml of ethanol is heated at reflux for 24 hours and then stirred at ambient temperature for an additional 36 hours. 100 ml of water are added, the ethanol is partially removed, the resulting mixture is extracted with ether and the combined ether extracts are extracted with 1N HCl. The aqueous solution is basified with an aqueous sodium hydroxide solution, extracted with ether, the combined ether extracts are dried, and the ether is removed, leaving a dark oil. The oil is dissolved in ether and ethereal hydrogen chloride is added to produce the sale which is collected by filtration, dried and recrystallized thrice from an ethanol-water mixture to give 4-(3-toluyl)piperidine hydrochloride, mp 196°-197° C.,

Workup

  1. temperatureat reflux for 24 hours
  2. customthe ethanol is partially removed
  3. extractionthe resulting mixture is extracted with ether
  4. extractionthe combined ether extracts are extracted with 1N HCl
  5. extractionextracted with ether
  6. dry with materialthe combined ether extracts are dried
  7. customthe ether is removed
  8. customleaving a dark oil
  9. customto produce the sale which
  10. filtrationis collected by filtration
  11. customdried
  12. customrecrystallized thrice from an ethanol-water mixture

Sources & evidence

ORD record
ord-16fe2b8288ba48178209a75f6fffad90
Source dataset
uspto-grants-1977_09
Patent number
US04046900

Reaction notes

Loading…