Sodium Iodide → HCID 56687105, compound

HRID 538752Notes

Reaction equation

HRID 538752 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH:5]([C:10]([OH:12])=[O:11])[CH2:4]1.[CH:13](N(C(C)C)CC)(C)C.[I-].[Na+].Cl.ClC[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1>CC#N.C(Cl)Cl>[O:9]=[C:6]1[CH2:7][CH2:8][N:3]([CH2:2][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH2:4][CH:5]1[C:10]([O:12][CH3:13])=[O:11]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 81531DiisopropylethylamineHCID 67328792HCID 67328792, compound

Product 1

HCID 56687105HCID 56687105, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

0.200 g (1.034 mmol) of 1-methyl-4-oxopiperidine-3-carboxylate hydrochloride (commercially available, ABCR), 0.54 mL (3.102 mmol) of diisopropylethylamine, 0.155 g (1.034 mmol) of sodium iodide and 0.170 g (1.034 mmol) of 3-(chloromethyl)pyridine hydrochloride were stirred at 80° C. in 5.0 mL of anhydrous CH3CN. The reaction was monitored by HPLC and UPLC-MS. After 1 h at 80° C., the insoluble inorganic materials were filtered off and the filtrate was concentrated in vacuo to give a yellowish residue. This residue was dissolved in CH2Cl2, washed with brine, H2O, dried over Na2SO4 and concentrated in vacuo to give pure methyl 4-oxo-1-(pyridin-3-ylmethyl)piperidine-3-carboxylate (0.257 g, 1.034 mmol, quantitative yield). The product was used for the next step without further manipulation.

Workup

  1. filtrationthe insoluble inorganic materials were filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give a yellowish residue
  4. washwashed with brine, H2O
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-83c67d5dbb1240549c4daa36b872a21e
Source dataset
uspto-grants-2014_10
Patent number
US08865758B2

Reaction notes

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