Water → 1-Formyl-4-(2-bromo-4-methoxyphenyl)piperazine

HRID 368827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 368827
[CH:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)=[O:2].C([O-])(=O)C.[Na+].[Br:22]Br.O>C(O)(=O)C>[CH:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[Br:22])[CH2:7][CH2:8]1)=[O:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 232887711-Formyl-4-(4-methoxyphenyl)piperazine2×

Produkt 1

HCID 232888181-Formyl-4-(2-bromo-4-methoxyphenyl)piperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

Sodium acetate (VI, 9.702 g, 0.1182 mol) is added to a mixture of 1-formyl-4-(4-methoxyphenyl)piperazine (VI, 5.17 g, 23.5 mmol) and acetic acid (102 ml). When the sodium acetate had completely dissolved, a solution of bromine (7.912 g, 49.5 mmol) in acetic acid (9.5 ml) is added over 14 min. After 35 min the mixture is poured into water and extracted exhaustively with dichloromethane. The combined organic extracts are backwashed with water, followed by saturated sodium bicarbonate, dried over sodium sulfate and concentrated. The residue is chromatographed on silica gel eluting first with ethyl acetate/dichloromethane (10/90) and then ethyl acetate/dichloromethane (20/80). The appropriate fractions are pooled and concentrated to give 1-formyl-4-(2-bromo-4-methoxyphenyl)piperazine (VII), NMR (CDCl3) 2.94, 3.55, 3.74, 3.78, 6.83, 6.97, 7.16 and 8.10 δ.

Aufarbeitung

  1. extractionextracted exhaustively with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel eluting first with ethyl acetate/dichloromethane (10/90)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8480e852e0574f6889d4ea8d97669abf
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133446

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