Triethylamine → 1′-(4-Nitrophenyl)-1,4′-bipiperidine

HRID 1091649Notes

Reaction equation

HRID 1091649 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[N:18]1([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>O1CCOCC1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:27]2[CH2:28][CH2:29][CH:24]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:25][CH2:26]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9590p-FluoronitrobenzeneHCID 786071,4'-Bipiperidine

Product 1

HCID 111300051′-(4-Nitrophenyl)-1,4′-bipiperidineYield 85.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-fluoro-4-nitrobenzene (1.3 mL, 12.3 mmol), triethylamine (6.0 mL; 43.0 mmol) and 4-(piperidin-1-yl)piperidine (2.36 g; 14.0 mmol) in dioxane (10 mL) was heated at reflux for 18 hr. After cooling to room temperature the mixture was concentrated under reduced pressure and the residue dissolved in DCM (150 mL). The DCM solution was washed with saturated aqueous sodium bicarbonate and brine, then dried over magnesium sulfate and concentrated under reduced pressure to produce a yellow solid. Hexanes were added and the suspension briefly sonicated. The solid was collected by filtration and washed with hexanes to give 1-(4-nitrophenyl)-4-(piperidin-1-yl)piperidine (3.05 g) as a yellow solid. A solution of 1-(4-nitrophenyl)-4-(piperidin-1-yl)piperidine (3.05 g; 10.5 mmol) in ethanol (20 mL) was hydrogenated at atmospheric pressure with 10% palladium on carbon (0.251 g) at room temperature for 17 hr. The mixture was filtered through diatomaceous earth and concentrated under reduced pressure to give 4-[4-(piperidin-1-yl)piperidin-1-yl]benzenamine (2.01 g) as a purple/pink solid.

Workup

  1. temperatureat reflux for 18 hr
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue dissolved in DCM (150 mL)
  4. washThe DCM solution was washed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto produce a yellow solid
  8. customthe suspension briefly sonicated
  9. filtrationThe solid was collected by filtration
  10. washwashed with hexanes

Sources & evidence

ORD record
ord-a069535de8cb443bab16a4bc36b3825a
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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