Triethylamine → 3-Phenyl[(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)methyl]benzene
Reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.Cl.[C:16]1([C:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:9]1([C:5]2[CH:4]=[C:3]([CH2:2][N:25]3[CH2:24][CH:23]=[C:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:27][CH2:26]3)[CH:8]=[CH:7][CH:6]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
Procedure
To a solution of 45 mg of 3-chloromethylbiphenyl in 5 mL of chloroform was added 50 mg of 4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride and 0.5 mL triethylamine. The reaction mixture was heated at reflux temperature overnight, cooled to room temperature, washed successively with 50 mL aliquots of dilute sodim hydroxide and brine. The chloroform was removed by evaporation under reduced pressure to yield 3-phenyl[(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)methyl]benzene which was purified by chromatography on silica gel using 5% methanol in dichloromethane as eluent. Evaporation of the solvent yielded a solid which was treated with ethereal-HCl to give 15 mg of 3-[(4-1,2,3,6-tetrahydropyridin-1-yl)methyl]biphenyl hydrochloride (Compound 3), mp 236-238° C.
Workup
- temperatureThe reaction mixture was heated
- temperatureat reflux temperature overnight
- washwashed successively with 50 mL aliquots of dilute sodim hydroxide and brine
- customThe chloroform was removed by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-6c82fe08edcb487cbf0e80f1f70bca91
- Source dataset
- uspto-grants-1999_06
- Patent number
- US05912350
Reaction notes
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