Acetonitrile → (E)-4-(4-phenoxyphenyl)-1-(3-phenyl-2-propenyl)-1,2,3,6-tetrahydropyridine

HRID 992364

Reaction equation

HRID 992364 reaction equation
C(#N)C.[O:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH:22]=2)=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:23](Br)[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(N(CC)CC)C>[O:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH2:22][CH2:21][N:20]([CH2:23]/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:19][CH:18]=2)=[CH:13][CH:12]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 98116BromomethylstyreneHCID 225999894-(4-Phenoxyphenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 15462121(E)-4-(4-phenoxyphenyl)-1-(3-phenyl-2-propenyl)-1,2,3,6-tetrahydropyridineYield 73%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To an 8 ml acetonitrile solution of 300 mg of the compound (8) synthesized in Example 1 were added 234 mg cinnamyl bromide and 0.5 ml of triethylamine. This was then heated and refluxed for 3 hours. To the reaction mixture was added 10 ml of ice water. This was then extracted with ethyl acetate. The extract was dried, filtered, then concentrated under reduced pressure to obtain a residue which was then purified by silica gel column chromatography (methylene chloride:methanol=25:1) to obtain the above-referenced compound (18) in an amount of 320 mg (yield 73%).

Workup

  1. temperatureThis was then heated
  2. temperaturerefluxed for 3 hours
  3. extractionThis was then extracted with ethyl acetate
  4. customThe extract was dried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a residue which
  8. customwas then purified by silica gel column chromatography (methylene chloride:methanol=25:1)

Sources & evidence

ORD record
ord-f40616ef35a64230b3a5f05529fe9d01
Source dataset
uspto-grants-2002_10
Patent number
US06469010B1

Linked notes

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