Triethylamine → N-{1-(R)-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropyl}-4-fluorobenzenesulfonamide

HRID 1610901

Reaktionsgleichung

Reaktionsgleichung von HRID 1610901
C(N(CC)CC)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.Cl.Cl.C[CH:22]1[N:27]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)[CH2:26][CH2:25][N:24]([CH2:37][CH:38]([NH:42]C(=O)C2C=CC(C)=CC=2)[CH:39]([CH3:41])[CH3:40])[CH2:23]1>C(Cl)Cl>[Cl:36][C:31]1[CH:30]=[C:29]([CH:34]=[CH:33][C:32]=1[Cl:35])[CH2:28][N:27]1[CH2:26][CH2:25][N:24]([CH2:37][C@H:38]([NH:42][S:15]([C:12]2[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH:39]([CH3:41])[CH3:40])[CH2:23][CH2:22]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 22257752n-{1(Rs)-[3-methyl-4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropyl}-4-methylbenzamide dihydrochloride salt

Produkt 1

HCID 18346059N-{1-(R)-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropyl}-4-fluorobenzenesulfonamideAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethylamine (21 ml, 0.15 mmol) and 4-fluorobenzenesulfonyl chloride (29 mg, 0.15 mmol) were added to a solution of 1-(R)-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropylamine (50 mg, 0.15 mmol) [prepared as described in Example 1 above] in methylene chloride (1.5 ml). The reaction mixture was stirred for 2 h, then concentrated. Purification by flash chromatography with 20:1 methylene: methanol as the eluant gave N-{1-(R)-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropyl}-4-fluorobenzenesulfonamide (49 mg) as a solid.

Aufarbeitung

  1. concentrationconcentrated
  2. customPurification by flash chromatography with 20:1 methylene

Quellen und Nachweise

ORD-Eintrag
ord-9c9a483654944f90833d4880c6e68a69
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06984637B2

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