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1-Cyclohexenylboronic acid → 1-(3-Cyclohex-1-enyl-4-nitro-phenyl)-4-methyl-piperazine

HRID 1043275
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1043275
Br[C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[C:18]1(B(O)O)[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]1([C:2]2[CH:3]=[C:4]([N:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)[CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 38629021-Cyclohexenylboronic acidHCID 117815411-(3-Bromo-4-nitrophenyl)-4-methylpiperazine

Produkt 1

HCID 591285801-(3-Cyclohex-1-enyl-4-nitro-phenyl)-4-methyl-piperazineAusbeute 123 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 102 mg (0.340 mmol) 1-(3-bromo-4-nitro-phenyl)-4-methyl-piperazine (as prepared in Example 9, step (a)), 59.7 mg (0.474 mmol) cyclohexen-1-ylboronic acid, 43.8 mg (0.0379 mmol) of tetrakis(triphenylphosphine)palladium (0) under Ar was treated with 206 μL (0.412 mmol) of 2.0 M degassed aq Na2CO3, 0.6 mL degassed anh toluene and 0.2 mL degassed anh EtOH and the mixture was heated at 100° C. for 21 h. After cooling to RT, the mixture was poured into EtOAc (10 mL), washed with brine (10 mL), dried (Na2SO4) and concentrated in vacuo. Chromatography on a 5-g silica SPE column with 1-3% EtOH in dichloromethane afforded 126 mg of the title compound (74% purity by RP-HPLC (C18 column) as a mixture with triphenylphosphine) as a yellow oil that was used in the following reaction without further purification. Mass spectrum (ESI, m/z): Calcd. for C17H23N3O3, 302.2 (M+H). found 302.2.

Aufarbeitung

  1. additionwas treated with 206 μL (0.412 mmol) of 2.0 M
  2. customdegassed aq Na2CO3, 0.6 mL
  3. customdegassed anh toluene and 0.2 mL
  4. customdegassed anh EtOH
  5. temperatureAfter cooling to RT
  6. additionthe mixture was poured into EtOAc (10 mL)
  7. washwashed with brine (10 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-09272bc8f5bf459796d9e71af163d6a1
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08557847B2

Notizen zur Reaktion

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