Hydrochloric Acid → HCID 19095547, compound

HRID 486438Notes

Reaction equation

HRID 486438 reaction equation
Cl.[CH3:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1(O)[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11]1.Cl>>[CH3:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 19095553HCID 19095553, compound

Product 1

HCID 19095547HCID 19095547, compoundYield 12%

Procedure

A mixture of 7 parts of 3-(2,3-dimethylphenyl)-1-(phenylmethyl)-3-piperidinol hydrochloride and 200 parts of a hydrochloric acid solution 6N was stirred and refluxed overnight. The reaction mixture was evaporated. Water was added and the base was liberated with ammonium hydroxide. The product was extracted with trichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and ethanol (98:2 by volume) as eluent. The first fraction was collected and the eluent was evaporated, yielding 0.7 parts (12%) of 5-(2,3-dimethylphenyl)-1,2,3,4-tetrahydro-1-(phenylmethyl)pyridine as a residue (intermediate 45).

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was evaporated
  3. additionWater was added
  4. extractionThe product was extracted with trichloromethane
  5. washThe extract was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and ethanol (98:2 by volume) as eluent
  11. customThe first fraction was collected
  12. customthe eluent was evaporated

Sources & evidence

ORD record
ord-3e11690be80c41ef8aabd9dc042c8204
Source dataset
uspto-grants-1994_03
Patent number
US05292738

Reaction notes

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