Potassium Carbonate → HCID 22677919, compound

HRID 1837493Notes

Reaction equation

HRID 1837493 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH2:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:16][C:17]1[N:22]=[C:21]([Cl:23])[C:20]([Cl:24])=[C:19](Cl)[C:18]=1[Cl:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:19]2[C:18]([Cl:26])=[C:17]([Cl:16])[N:22]=[C:21]([Cl:23])[C:20]=2[Cl:24])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16584PentachloropyridineHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 22677919HCID 22677919, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-Boc-4-(aminomethyl)piperidine (2.0 g, 9.33 mmol), pentachloropyridine (2.58 g, 10.3 mmol) and potassium carbonate (2.58 g, 18.7 mmol) was heated at 60° C. in DMF (22 mL) for 2 h. Excess DMF was removed in vacuo and the residue taken in to water/ethyl acetate. The aqueous solution was extracted with ethyl acetate (×3) and the combined organic solution dried (MgSO4) and concentrated in vacuo. Flash chromatography (SiO2, hexane/diethyl ether 30% to 60% gave the product as a white solid (2.5 g, 62%).

Workup

  1. customExcess DMF was removed in vacuo
  2. extractionThe aqueous solution was extracted with ethyl acetate (×3)
  3. dry with materialthe combined organic solution dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6d52bc5c9fc4bb8b0f72bbbd51d8edf
Source dataset
uspto-grants-2004_08
Patent number
US06784182B2

Reaction notes

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