1-Methylpiperazine → HCID 86713635, Verbindung

HRID 1257195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257195
Br[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[F:12].[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.CCN(C(C)C)C(C)C>C1COCC1>[F:12][C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[CH2:2][N:17]1[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]1

Komponenten

5

Edukt 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 103539672-(Bromomethyl)-1-fluoro-4-nitrobenzene

Produkt 1

HCID 86713635HCID 86713635, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of ˜80% pure 2-(bromomethyl)-1-fluoro-4-nitrobenzene (0.956 g, 3.27 mmol) in THF (10 mL) was added slowly drop-wise to a −20° C. solution of 1-methylpiperazine (0.393 g, 3.92 mmol) and DIEA (1.142 mL, 6.54 mmol) in THF (20 mL), the mixture allowed to warm slowly to RT and stirred overnight. The resulting solid was removed via filtration and the filtrate was concentrated to dryness and purified via silica gel chromatography (EtOAc, MeOH/DCM) to afford 1-(2-fluoro-5-nitrobenzyl)-4-methylpiperazine (577 mg, 70% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.28 (dd, J=6.2, 3.0 Hz, 1H), 8.21 (ddd, J=9.0, 4.4, 3.0 Hz, 1H), 7.47 (t, J=9.1 Hz, 1H), 3.60 (s, 2H), 2.48-2.25 (br m, 8H), 2.14 (s, 3H); MS (ESI) m/z: 254.1 [M+H]+.

Aufarbeitung

  1. customThe resulting solid was removed via filtration
  2. concentrationthe filtrate was concentrated to dryness
  3. custompurified via silica gel chromatography (EtOAc, MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-7e9e6a23866c43609964214a776726e6
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461179B1

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