1-Chloro-4-(chloromethyl)benzene → HCID 2838484, Verbindung

HRID 1280981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1280981
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[NH:19]1[CH2:29][CH2:28][CH2:27][CH:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20]1>CC#N>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:19]2[CH2:29][CH2:28][CH2:27][CH:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 81531DiisopropylethylamineHCID 98969Ethyl nipecotate

Produkt 1

HCID 2838484HCID 2838484, VerbindungAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

4-Chlorobenzyl chloride (6.42 g, 39.9 mmol) and iPr2NEt (7.74 g, 40.0 mmol) were added to a solution of ethyl nipecotate (6.29 g, 40.0 mmol) in CH3CN (15 mL). The reaction mixture was stirred at 70° C. for 1.5 h. The solvent was removed under reduced pressure. Saturated aqueous NaHCO3 (50 mL) was added to the residue and the mixture was extracted with EtOAc (100 mL). The organic phase was washed with saturated aqueous NaHCO3 and brine, and dried over Na2SO4. The solvent was removed under reduced pressure to afford ethyl 1-(4-chlorobenzyl)nipecotate as a red yellow oil (11.025 g, 97.8%) used without further purification. The purity was determined by RPLC/MS (97%); ESI/MS m/e 382.2 (M++H, C15H21ClNO2).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionSaturated aqueous NaHCO3 (50 mL) was added to the residue
  3. extractionthe mixture was extracted with EtOAc (100 mL)
  4. washThe organic phase was washed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7c2b7ce1b6664d529b62f4baee199866
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451842B1

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