1,2,3,6-Tetrahydro-1-(4-nitrophenyl)-4-phenylpyridine → HCID 22494681, compound

HRID 1816731Notes

Reaction equation

HRID 1816731 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)C.O1CCCC1.[Pd]>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([N:10]2[CH2:9][CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12][CH2:11]2)=[CH:18][CH:17]=1

Participants

6

Reactant 2

HCID 47810351,2,3,6-Tetrahydro-1-(4-nitrophenyl)-4-phenylpyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 22494681HCID 22494681, compoundYield 98.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)nitrobenzene (6.4 g) in ethyl alcohol (192 ml) and tetrahydrofuran (192 ml) was added 10% palladium on carbon (0.64 g), and hydrogen gas at atmosphere pressure for 6 hours. The reaction mixture was filtered through celite and evaporated under reduced pressure to give 1-(4-aminophenyl)-4-phenylpiperidine (5.66 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-00f7a174069a4ce2a0b76bd0f71fb554
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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