Diethyl Ether → HCID 87618670, compound

HRID 2111425Notes

Reaction equation

HRID 2111425 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=1.CCOCC.C(=O)(O)[O-].[K+]>O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:15]2[C:16]([N+:20]([O-:22])=[O:21])=[CH:17][N:18]=[C:13]([Cl:12])[N:14]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 98969Ethyl nipecotateHCID 516893Potassium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 87618670HCID 87618670, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3.16 g (0.02 mole) of piperidine-3-carboxylic acid ethyl ester, 3.71 g (0.019 mole) of 2,4-dichloro-5-nitro-pyrimidine and 60 mL of ether at 5 degrees, was added a solution of 4 g (0.04 mole) of potassium bicarbonate in 40 mL of water was added over 25 minutes. The mixture was stirred for an additional 1 hour, then extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with hexanes-ethyl acetate (100:0-88:12) to give 3.99 g of (rac)-1-(2-chloro-5-nitro-pyrimidin-4-yl)-piperidine-3-carboxylic acid ethyl ester (IV-67).

Workup

  1. additionwas added over 25 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with hexanes-ethyl acetate (100:0-88:12)

Sources & evidence

ORD record
ord-7a9a7f742b224fa8a33d612c4b885819
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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