Dichloromethane → Methyl 4-(1-(naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoate

HRID 1881686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881686
CO[C:3]1[CH:8]=[C:7](C)[C:6]([S:10](Cl)(=[O:12])=[O:11])=[C:5]([CH3:14])[CH:4]=1.CCN([CH2:20][CH3:21])CC.Cl.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33].[CH2:36](Cl)Cl>>[C:6]1([S:10]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]2[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])(=[O:11])=[O:12])[C:5]2[C:4](=[CH:36][CH:20]=[CH:21][CH:14]=2)[CH:3]=[CH:8][CH:7]=1

Komponenten

5

Edukt 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chlorideHCID 66772062Methyl 4-(piperidin-2-yl)butanoate hydrochloride

Produkt 1

HCID 57904267Methyl 4-(1-(naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoateAusbeute 79 %

Versuchsvorschrift

The sulfonyl chloride 1 (9.76 g, 85.2 mmol) and Et3N (11.8 ml, 85.2 mmol) were dissolved in CH2Cl2 (100 ml), and a solution of diphenylmethanamine (2, 15.61 g, 85.2 mmol) in CH2Cl2 (40 ml) was added dropwise in the course of 10 min. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was washed with aqueous 0.5 M KHSO4 (2×200 ml) and sat. NaCl solution (100 ml), dried over Na2SO4 and concentrated to dryness. Recrystallization from CH2Cl2 at 0-5° C. gave 17.63 g (79%) of the sulfonamide 3.

Aufarbeitung

  1. washThe reaction mixture was washed with aqueous 0.5 M KHSO4 (2×200 ml) and sat. NaCl solution (100 ml)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customRecrystallization from CH2Cl2 at 0-5° C.

Quellen und Nachweise

ORD-Eintrag
ord-cf7f4129a0f24a0b98daca5c89f6ae79
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318769B2

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