1-Iodopentane → N,N-bis(pyridin-2-ylmethyl)pentan-1-amine

HRID 1926524

Reaktionsgleichung

Reaktionsgleichung von HRID 1926524
[OH-].[K+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.I[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CN(C)C=O>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Komponenten

5

Edukt 3

HCID 123351-Iodopentane2×HCID 14797Potassium HydroxideHCID 73759Bis(2-pyridylmethyl)amine

Produkt 1

HCID 58794716N,N-bis(pyridin-2-ylmethyl)pentan-1-amineAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 15 ml of N,N-dimethylformamide, 0.85 g potassium hydroxide, 1.0 g di(2-picolyl)amine, and 0.99 g 1-iodopentane were successively added. The mixture was stirred under nitrogen at 35 C for 2.5 hours before an additional 0.99 g 1-iodopentane were added. The mixture was then stirred for 16 hrs at 35 C under nitrogen. The reaction was quenched with 90 ml of water and extracted with two 50 ml portions of ethyl acetate. The combined organic layers were washed with two 25 ml portions of water, dried over anhydrous magnesium sulfate, and filtered. Following solvent removal, the orange oil obtained was purified by silica gel chromatography using a methanol/ethyl acetate mixed solvent system that was ramped from 0% to 10% methanol by volume during the course of the elution. An orange oil (0.98 g) was obtained.

Aufarbeitung

  1. additionwere added
  2. customThe reaction was quenched with 90 ml of water
  3. extractionextracted with two 50 ml portions of ethyl acetate
  4. washThe combined organic layers were washed with two 25 ml portions of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customFollowing solvent removal
  8. customthe orange oil obtained
  9. customwas purified by silica gel chromatography
  10. washwas ramped from 0% to 10% methanol by volume during the course of the elution

Quellen und Nachweise

ORD-Eintrag
ord-4ddc1cc6fcb04b71b859aad11dd6aebc
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08182718B2

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