Diethyl Ether → 4-(4-Benzylpiperazin-1-yl)-2-[(Phenylsulfonyl)methyl]aniline

HRID 1292982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1292982
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([CH2:23][S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn].C([O-])(O)=O.[Na+].CCOCC>CO.Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([CH2:23][S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 5352426Tin atomHCID 442428861-Benzyl-4-{4-nitro-3-[(phenylsulfonyl)methyl]phenyl}piperazine

Produkt 1

HCID 589047884-(4-Benzylpiperazin-1-yl)-2-[(Phenylsulfonyl)methyl]anilineAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A mixture of 1-benzyl-4-{4-nitro-3-[(phenylsulfonyl)methyl]phenyl}piperazine (6.77 g, 15.0 mmol) and granular tin (7.48 g, 63.0 mmol) in methanol and conc. hydrochloric acid is heated at 45° C. for 4 h, stirred at ambient temperature for 18 h, carefully poured into saturated aqueous NaHCO3, treated with ether and stirred for 0.5 h. The phases are separated and the aqueous phase is extracted sequentially with ether and CH2Cl2. The extracts and organic phase are combined, dried over MgSO4 and concentrated in vacuo. The resultant residue is dissolved in CH2Cl2 and filtered through Celite®. The filtrate is concentrated in vacuo to afford the title compound as a pale yellow solid, 6.11 g (97% yield), mp 141–143° C., characterized by NMR and mass spectral analyses

Aufarbeitung

  1. stirringstirred for 0.5 h
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted sequentially with ether and CH2Cl2
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resultant residue is dissolved in CH2Cl2
  7. filtrationfiltered through Celite®
  8. concentrationThe filtrate is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fdd708a8b416450db135943a35f06014
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238696B2

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