Hydrochloric Acid → HCID 19095547, compound
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]=1Participants
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 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
- temperaturerefluxed overnight
- customThe reaction mixture was evaporated
- additionWater was added
- extractionThe product was extracted with trichloromethane
- washThe extract was washed with water
- customdried
- filtrationfiltered
- customevaporated
- customThe residue was purified by column chromatography over silica gel using
- additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
- customThe first fraction was collected
- customthe eluent was evaporated
Sources & evidence
- ORD record
- ord-4a8929192bfc4816912f84e9fb719816
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05157035
Reaction notes
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