Lithium Hydroxide → 1-(4-chlorobenzyl)nipecotic acid

HRID 1280982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1280982
[Li+].[OH-].[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([CH2:8][N:9]2[CH2:19][CH2:18][CH2:17][CH:11]([C:12]([O:14]CC)=[O:13])[CH2:10]2)=[CH:6][CH:5]=1>O.C1COCC1.CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[CH2:19][CH2:18][CH2:17][CH:11]([C:12]([OH:14])=[O:13])[CH2:10]2)=[CH:20][CH:21]=1

Komponenten

6

Edukt 2

HCID 3939Lithium HydroxideHCID 2838484HCID 2838484, Verbindung

Produkt 1

HCID 35450941-(4-chlorobenzyl)nipecotic acidAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of LiOH (1.66 g) in H2O (25 mL) was added to the solution of ethyl 1-(4-chlorobenzyl)nipecotate in THF (60 mL) and CH3OH (20 mL). The reaction mixture was stirred at room temperature for 15 h. The solvent was removed under reduced pressure to afford an amorphous solid which was purified by column chromatography (SiO2, 50% CH3OH—CH2Cl2) to yield 1-(4-chlorobenzyl)nipecotic acid (9.75 g, 98.2%) as a pale yellow amorphous solid. The purity was determined by RPLC/MS (>95%); ESI/MS m/e 254.0 (M++H, C13H17ClNO2).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customto afford an amorphous solid which
  3. customwas purified by column chromatography (SiO2, 50% CH3OH—CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-b0300ce4b5f9405785cfce6a1a9e4ccf
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451842B1

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