4-Isopropoxyaniline → 1-(Butyl sulfonyl)-N-(4-isopropoxyphenyl)piperidine-3-carboxamide

HRID 1931291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1931291
Cl.CN(C)CCCN=C=NCC.[CH2:13]([S:17]([N:20]1[CH2:25][CH2:24][CH2:23][CH:22]([C:26]([OH:28])=O)[CH2:21]1)(=[O:19])=[O:18])[CH2:14][CH2:15][CH3:16].[CH:29]([O:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1)([CH3:31])[CH3:30]>N1C=CC=CC=1>[CH2:13]([S:17]([N:20]1[CH2:25][CH2:24][CH2:23][CH:22]([C:26]([NH:37][C:36]2[CH:35]=[CH:34][C:33]([O:32][CH:29]([CH3:31])[CH3:30])=[CH:39][CH:38]=2)=[O:28])[CH2:21]1)(=[O:18])=[O:19])[CH2:14][CH2:15][CH3:16]

Komponenten

5

Edukt 3

HCID 821124-IsopropoxyanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162282211-(Butylsulfonyl)piperidine-3-carboxylic acid

Produkt 1

HCID 454825031-(Butyl sulfonyl)-N-(4-isopropoxyphenyl)piperidine-3-carboxamideAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (57.5 mg, 0.3 mmol) was added to a pyridine (5 mL) solution of the compound (50 mg, 0.2 mmol) synthesized in (1) and 4-isopropoxyaniline (0.061 mg, 0.4 mmol), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and, after addition of ethyl acetate, washed once with 1N-sodium hydroxide solution, and once with saturated brine. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was then purified using silica gel column chromatography to obtain the title compound (33 mg, 43%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionafter addition of ethyl acetate
  3. washwashed once with 1N-sodium hydroxide solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was then purified

Quellen und Nachweise

ORD-Eintrag
ord-1d68ae452b904c4b82a8f9b6ec5a80c4
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188280B2

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