Isopropyltriphenylphosphonium iodide → 1-Benzyl-4-[N-methyl-N-(3-(2-methyl-1-propenyl)-2-pyridinyl)amino]piperidine

HRID 361794Notes

Reaction equation

HRID 361794 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[I-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)C.[CH2:29]([N:36]1[CH2:41][CH2:40][CH:39]([N:42]([CH3:51])[C:43]2[C:48]([CH:49]=O)=[CH:47][CH:46]=[CH:45][N:44]=2)[CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[CH2:29]([N:36]1[CH2:41][CH2:40][CH:39]([N:42]([CH3:51])[C:43]2[C:48]([CH:49]=[C:2]([CH3:3])[CH3:1])=[CH:47][CH:46]=[CH:45][N:44]=2)[CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 2723783Isopropyltriphenylphosphonium iodideHCID 108287021-Benzyl-4-[N-methyl-N-(3-(formyl)-2-pyridinyl)amino]piperidineHCID 178418339Butyllithium

Product 1

HCID 106645461-Benzyl-4-[N-methyl-N-(3-(2-methyl-1-propenyl)-2-pyridinyl)amino]piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyl lithium (1.6M, 8.1 ml, 12.93 mmol) is added to a suspension of isopropyltriphenylphosphonium iodide (5.6 g, 12.93 mmol) in dry THF. The ylide is allowed to generate for 45 min at 20°-25° under nitrogen before a solution of 1-benzyl-4-[N-methyl-N-(3-(formyl)-2-pyridinyl)amino]piperidine (XXI, EXAMPLE 13, 2.0 g, 6.5 mmol) in dry THF is added. The reaction is stirred an additional 30 min before being quenched with water and extracted with chloroform. The extracts are washed with saline and dried (sodium sulfate). Removal of the solvent gives a residue which is chromatographed (silica gel, 4×35 cm column; ethyl acetate/hexane (1/3→1/1) to give the title compound, NMR (300 MHz, CDCl3) 1.55-1.65, 1.74, 1.79-1.85, 1.85, 2.75, 2.87-2.90, 3.40-3.48, 3.42, 5.97, 6.69, 7.16-7.28 and 8.04δ.

Workup

  1. additionis added
  2. custombefore being quenched with water
  3. extractionextracted with chloroform
  4. washThe extracts are washed with saline
  5. dry with materialdried (sodium sulfate)
  6. customRemoval of the solvent
  7. customgives a residue which
  8. customis chromatographed (silica gel, 4×35 cm column

Sources & evidence

ORD record
ord-60e98b503143446fb65a4ae876e7add8
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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