Potassium Iodide → HCID 12082300, compound

HRID 1358693Notes

Reaction equation

HRID 1358693 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]1)=[O:5])[CH3:2].Cl.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C1N2CCN(CC2)C1>CN(C=O)C.O>[CH2:1]([O:3][C:4]([C:6]1([CH2:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=2)[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:7]1)=[O:5])[CH3:2]

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 9237DabcoHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 64208761-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylate

Product 1

HCID 12082300HCID 12082300, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (10.34 g, 38.2 mmol) in DMF (40 mL) at about 0° C. was added picolyl chloride hydrochloride (5.7 g, 34.7 mmol), potassium carbonate (14.4 g, 104.1 mmol) and potassium iodide (5.76 g, 34.7 mmol). After stirring at about 0° C. for about 2 hours, the ice bath was removed and DABCO (973 mg, 8.68 mmol) was added. The reaction mixture was stirred for about 30 min. and poured into a mixture of water and IPE. The organic layer was separated and washed with saturated aqueous NaHCO3 and saturated aqueous NaCl, dried over Na2SO4 and concentrated in vacuo. The crude residue was crystallized from hexanes to give a white solid (8.19 g, yield 65%). 1H-NMR (CDCl3) δ 1.17 (t, 3H), 1.48 (s, 9H), 1.55 (s, 2H), 2.61 (m, 1H), 2.71 (m, 1H), 3.31-3.50 (m, 3H), 4.11 (d, 2H), 4.49 (d, 1H), 7.06 (brs, 1H), 7.17 (d, 1H), 7.54 (m, 1H), 8.40 (s, 1H).

Workup

  1. customthe ice bath was removed
  2. stirringThe reaction mixture was stirred for about 30 min.
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous NaHCO3 and saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was crystallized from hexanes

Sources & evidence

ORD record
ord-9ee38327ed65494bb43087b06776512e
Source dataset
uspto-grants-2003_07
Patent number
US06596867B2

Reaction notes

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