Isopropyl iodide → 1-Isopropyl-4-(4-nitrophenyl)piperidine

HRID 1783984Notes

Reaction equation

HRID 1783984 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].I[CH:23]([CH3:25])[CH3:24]>C(#N)C>[CH:23]([N:13]1[CH2:12][CH2:11][CH:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:15][CH2:14]1)([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 159258174-(4-Nitrophenyl)piperidine

Product 1

HCID 574241751-Isopropyl-4-(4-nitrophenyl)piperidineYield 99.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(4-Nitrophenyl)piperidine (250 mg, 1.21 mmol), K2CO3 (170 mg, 1.21 mmol) and 2-iodopropane (240 μL, 2.4 mmol) are stirred in acetonitrile (3 mL) in a sealed tube at 120° C. for 45 min. The mixture is cooled and the solvent removed under reduced pressure. The residue is partitioned between DCM (20 mL) and water (5 mL), the layers are separated and the DCM is washed with water (5 mL) and brine (5 mL) and dried over MgSO4. Evaporation of the solvent affords the title compound (300 mg) which is used without further purification.

Workup

  1. temperatureThe mixture is cooled
  2. customthe solvent removed under reduced pressure
  3. customThe residue is partitioned between DCM (20 mL) and water (5 mL)
  4. customthe layers are separated
  5. washthe DCM is washed with water (5 mL) and brine (5 mL)
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-66a7e911dae54a91aadb01fdc0782deb
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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