Acetic Acid → 1-(2-Bromophenyl)-4-cyclopropylmethylpiperazine

HRID 32269

Reaktionsgleichung

Reaktionsgleichung von HRID 32269
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(O)(=O)C.[CH:18]1([CH:21]=O)[CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:21][CH:18]2[CH2:20][CH2:19]2)[CH2:10][CH2:9]1

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 123114CyclopropanecarboxaldehydeHCID 27571531-(2-Bromophenyl)piperazineHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 231428391-(2-Bromophenyl)-4-cyclopropylmethylpiperazineAusbeute 103,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-(2-bromophenyl)piperazine (3.0 g, 12.4 mmol) in tetrahydrofuran (30 mL) were added acetic acid (0.71 mL, 12.4 mmol), cyclopropanecarbaldehyde (1.39 mL, 18.66 mmol) and sodium triacetoxyborohydride (4.22 g, 19.9 mmol), followed by stirring for 88 hours at room temperature. Aqueous solution of potassium carbonate was added to the reaction mixture, extraction was performed with ethyl acetate, and the organic layer was concentrated. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 3.773 g of the title compound as a colorless oil.

Aufarbeitung

  1. concentrationthe organic layer was concentrated
  2. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-c185f7e84db146ab9a55b333dfe511a7
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425554B2

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