p-Fluoronitrobenzene → 1,2,3,6-Tetrahydro-1-(4-nitrophenyl)-4-phenylpyridine

HRID 1452779Notes

Reaction equation

[C:1]1([C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.C([O-])([O-])=O.[K+].[K+].F[C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[N+:35]([C:32]1[CH:33]=[CH:34][C:29]([N:10]2[CH2:9][CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11]2)=[CH:30][CH:31]=1)([O-:37])=[O:36]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 0.5 g (2.5 mmole) of 4-phenyl-1,2,3,6-tetrahydropyridine, 0.51 ml (2.8 mmole) of diisopropylethylamine, 0.71 g (5 mmole) of K2CO3, 0.40 g ((2.8 mmole) of 4-fluoronitrobenzene in 10 ml of DMF is heated at 100° C., for 24 hours. At the end of the reaction, the mixture is poured into 25 ml of a saturated solution of NaHCO3 and the product is extracted using 25 ml of AcOEt. After decantation, the organic solution is washed twice with 20 ml of water followed by 20 ml of brine, drying over magnesium sulphate, filtration and evaporation of the solvent under vacuum produce a yellow solid with a yield of 42%. Melting point: 185-192° C. (decomposition).

Workup

customAt the end of the reaction
extractionthe product is extracted
washAfter decantation, the organic solution is washed twice with 20 ml of water
dry with materialdrying over magnesium sulphate, filtration and evaporation of the solvent under vacuum
customproduce a yellow solid with a yield of 42%

Sources & evidence

ORD record: ord-3438d1070b8c492aa63396454fd34f3e
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473779B2

Reaction notes

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