Methanesulfonyl chloride → 1-{1-[3-(Methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazine

HRID 419366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419366
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:13][CH2:14][CH:15]([N:18]3[CH2:19][CH2:20][N:21]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:22][CH2:23]3)[CH2:16][CH2:17]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 598602641-{1-[3-(Methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine

Produkt 1

HCID 598602451-{1-[3-(Methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazineAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 1-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine (Example 57, step C) (5.0 g, 11.6 mmol), methane sulfonyl chloride (1.4 mL, 17.5 mmol) and DCM (200 mL) was added TEA (80.1 mL, 58.2 mmol). The reaction was stirred at rt and monitored by TLC. After complete consumption of the starting material the clear yellow solution was concentrated onto silica gel and purified by chromatography to afford the title compound of step A as a yellow solid (3.54 g, 76%). 1H NMR (400 MHz, DMSO-d6) δ 7.85 (d, J=9.5 Hz, 1H), 6.57 (dd, J=9.2, 2.6 Hz, 1H), 6.48 (d, J=2.6 Hz, 1H), 4.09-4.00 (m, 2H), 3.89 (s, 3H), 3.10-3.03 (m, 4H), 2.99-2.90 (m, 2H), 2.84 (s, 3H), 2.61-2.52 (m, 5H), 1.85-1.77 (m, 2H), 1.50-1.37 (m, 2H).

Aufarbeitung

  1. customAfter complete consumption of the starting material the clear yellow solution
  2. concentrationwas concentrated onto silica gel
  3. custompurified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-de03ff5ef7ce4d00bc8d061a558ea14d
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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