Hydrochloric Acid → HCID 19095547, compound

HRID 359410Notes

Reaction equation

HRID 359410 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 6 N 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 methanol (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). The second fraction was collected and the eluent was evaporated, yielding 5.3 parts (91%) of 5-(2,3-dimethylphenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)pyridine as a residue (intermediate 46).

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 methanol (98:2 by volume) as eluent
  11. customThe first fraction was collected
  12. customthe eluent was evaporated

Sources & evidence

ORD record
ord-bdfaa491fcca40efb62506cb1cf25143
Source dataset
uspto-grants-1991_03
Patent number
US05001125

Reaction notes

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