Lithium Hydroxide → 4-(1-Benzenesulfonylpiperidin-4-ylmethyl)-phenylamine

HRID 993411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 993411
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH2:15][CH2:14]2)=[CH:8][CH:7]=1)=O.[OH-].[Li+]>CO.O>[C:22]1([S:19]([N:16]2[CH2:17][CH2:18][CH:13]([CH2:12][C:9]3[CH:8]=[CH:7][C:6]([NH2:5])=[CH:11][CH:10]=3)[CH2:14][CH2:15]2)(=[O:20])=[O:21])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 218770242,2,2-trifluoro-N-(4-(1-benzenesulfonyl-piperidin-4-ylmethyl)-phenyl]acetamide

Produkt 1

HCID 218770334-(1-Benzenesulfonylpiperidin-4-ylmethyl)-phenylamineAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2,2,2-trifluoro-N-[4-(1-benzenesulfonylpiperidin-4-ylmethyl)-phenyl]acetamide (0.45 g) and lithium hydroxide (0.23 g) in methanol (10 mL) and water (1 mL) was stirred for about 48 hours. The reaction mixture was concentrated in vacuo, diluted with cold water, and extracted with dichloromethane. The organic layer was washed with cold water and brine, dried, and solvents removed in vacuo. The residue was crystallized from ethyl acetate/hexanes to give 4-(1-benzenesulfonylpiperidin-4-ylmethyl)-phenylamine (0.29 g, 83%), m.p. 158° C.; Analysis for C18H22N2O2S: Calc.: C, 65.43; H, 6.71; N, 8.48; Found: C, 65.59; H, 6.61; N, 8.66.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with cold water
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with cold water and brine
  5. customdried
  6. customsolvents removed in vacuo
  7. customThe residue was crystallized from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-12b9277627944cb1b1667504779b9ad2
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06472536B1

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