Hydrochloric Acid → N-ethyl-3-methyl-4-(piperazin-1-yl)benzamide hydrochloride

HRID 874540

Reaktionsgleichung

Reaktionsgleichung von HRID 874540
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)=[C:8]([CH3:25])[CH:7]=1)=[O:5])[CH3:2].[ClH:26]>O1CCOCC1.C(OCC)C>[ClH:26].[CH2:1]([NH:3][C:4](=[O:5])[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)=[C:8]([CH3:25])[CH:7]=1)[CH3:2]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 58324366Tert-butyl 4-(4-(ethylcarbamoyl)-2-methylphenyl)piperazine-1-carboxylate

Produkt 1

HCID 66775291N-ethyl-3-methyl-4-(piperazin-1-yl)benzamide hydrochlorideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Tert-butyl 4-(4-(ethylcarbamoyl)-2-methylphenyl)piperazine-1-carboxylate (0.9323 g, 2.68 mmol) was diluted with 4.0M HCl in dioxane (8 mL) and stirred for 30 min. The thick white precipitate that formed was diluted with ethyl ether (10 mL) and stirred until a fine suspension resulted. The precipitate was filtered under nitrogen, washed with ether (5 mL) and dried in vacuo to afford N-ethyl-3-methyl-4-(piperazin-1-yl)benzamide hydrochloride (0.7528 g, 2.65 mmol, 99% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (t, J=7.20 Hz, 3 H) 2.29 (s, 3 H) 3.00-3.14 (m, 4 H) 3.16-3.32 (m, 6 H) 7.07 (d, J=8.34 Hz, 1 H) 7.62-7.71 (m, 2 H) 8.34 (t, J=5.43 Hz, 1 H) 9.17 (br. s., 2 H). ESI-MS: m/z 248.2 (M+H)+.

Aufarbeitung

  1. customThe thick white precipitate that formed
  2. stirringstirred until a fine suspension
  3. customresulted
  4. filtrationThe precipitate was filtered under nitrogen
  5. washwashed with ether (5 mL)
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-05006f1f63774951803f62941bf19759
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980902B2

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