Pyridine → 2-[4-(Hexadecyloxy)phenoxy]-N-[2-(2-pyridinyl)ethyl]acetamide

HRID 1728870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1728870
[CH2:1]([O:17][C:18]1[CH:28]=[CH:27][C:21]([O:22][CH2:23][C:24](Cl)=[O:25])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[NH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:1]([O:17][C:18]1[CH:28]=[CH:27][C:21]([O:22][CH2:23][C:24]([NH:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[O:25])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 759192-PyridineethanamineHCID 516892Sodium BicarbonateHCID 104317244-Hexadecyloxyphenoxyacetic chloride

Produkt 1

HCID 197646782-[4-(Hexadecyloxy)phenoxy]-N-[2-(2-pyridinyl)ethyl]acetamideAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 0° C. solution of 2.3 g of product from Example 87 in 50 ml of methylene chloride is added, dropwise, 0.72 g of 2-(2-aminoethyl)pyridine followed by 1.77 g of pyridine. The reaction is stirred at room temperature for 16 hours, poured into chloroform and saturated sodium bicarbonate and extracted with chloroform. The combined chloroform layers are washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 75% ethyl acetate/hexane) to give 2.2 g of the desired product as a colorless solid.

Aufarbeitung

  1. extractionextracted with chloroform
  2. washThe combined chloroform layers are washed with saturated sodium chloride
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography (silica gel: 75% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d16a0de467e646fb9568d14b69fdace8
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05328921

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