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Potassium Hydroxide → HCID 24990093, Verbindung

HRID 2054170
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2054170
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[CH2:22][CH2:21][CH:20]([C:23]4[CH:24]=[C:25]([NH:30]C(OCC5C=CC=CC=5)=O)[CH:26]=[CH:27][C:28]=4[CH3:29])[CH2:19][CH2:18]3)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[OH-].[K+].CCCCCC.CCOC(C)=O>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][N:17]3[CH2:22][CH2:21][CH:20]([C:23]4[CH:24]=[C:25]([NH2:30])[CH:26]=[CH:27][C:28]=4[CH3:29])[CH2:19][CH2:18]3)=[CH:14][CH:15]=2)=[CH:5][CH:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 21226206Ethyl acetate hexaneHCID 69115453HCID 69115453, Verbindung

Produkt 1

HCID 24990093HCID 24990093, VerbindungAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

N-[3-(1-{[4-(4-methoxyphenylthio)phenyl]methyl}(4-piperidyl))-4-methylphenyl] (phenylmethoxy)carboxamide (486 mg, 0.881 mmol) was dissolved in methanol (10.0 mL) and a KOH solution (40%, 1.20 mL) was added. The reaction mixture was heated at 100° C. for 10 h. After cooling to room temperature, the reaction mixture was poured into a separatory funnel. The phases were separated and the aqueous phase was extracted with CH2Cl2 (2×20 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash column chromatography (eluent: Hexane:EtOAc (1:1 then 1:4)) gave 3-(1-{[4-(4-methoxyphenylthio)phenyl]methyl}(4-piperidyl))-4-methylphenylamine (362 mg, 98.2% yield). 1H NMR (400 MHz; CDCl3) δ 7.43-7.35 (m, 4H), 7.24-7.11 (m, 3H), 6.93-6.85 (m, 2H), 6.63-6.58 (m, 1H), 6.48-6.42 (m, 1H), 3.82 (s, 3H), 3.48 (s, 2H), 3.03-2.91 (m, 2H), 2.68-2.54 (m, 1H), 2.20 (s, 3H), 2.13-1.98 (m, 2H), 1.79-1.64 (m, 4H). ESMS m/e: 419.2 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. additionthe reaction mixture was poured into a separatory funnel
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2 (2×20 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash column chromatography (eluent

Quellen und Nachweise

ORD-Eintrag
ord-cc6f680eefac43a0bf7a8ed788238f84
Quelldatensatz
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07329656B2

Notizen zur Reaktion

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