1-(1-Methyl-4-piperidinyl)piperazine → 2-[1-(4-Methoxy-2,6-dimethyl-phenylsulfonyl)-piperidin-2-ylmethoxy]-1-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-ethanone

HRID 2090805

Reaktionsgleichung

Reaktionsgleichung von HRID 2090805
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH2:19][O:20][CH2:21][C:22](O)=[O:23])(=[O:12])=[O:11])=[C:5]([CH3:25])[CH:4]=1.[CH3:26][N:27]1[CH2:32][CH2:31][CH:30]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:29][CH2:28]1>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH2:19][O:20][CH2:21][C:22]([N:36]2[CH2:35][CH2:34][N:33]([CH:30]3[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]3)[CH2:38][CH2:37]2)=[O:23])(=[O:12])=[O:11])=[C:5]([CH3:25])[CH:4]=1

Komponenten

4

Edukt 2

HCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 574368002-((1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetic acid

Produkt 1

HCID 249455742-[1-(4-Methoxy-2,6-dimethyl-phenylsulfonyl)-piperidin-2-ylmethoxy]-1-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

N,N′-Carbonyldiimidazole (114 mg, 0.706 mmol) was added to a solution of 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetic acid (250 mg, 0.673 mmol) in dichloromethane (15 ml), and the mixture was stirred for 1 h at room temperature. A solution of 1-(1-methylpiperidin-4-yl)piperazine (123 mg, 0.673 mmol) in dichloromethane (5 ml) was then added, and the reaction mixture was stirred for 15 h at room temperature. The reaction mixture was then extracted with water (20 ml) and saturated sodium chloride solution (20 ml), and the organic phase was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography using dichloromethane/methanol (97:3→90:10).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 15 h at room temperature
  2. extractionThe reaction mixture was then extracted with water (20 ml) and saturated sodium chloride solution (20 ml)
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6601b9ab513848f6b96a0bce5eed963b
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08435978B2

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