Phosphorus oxychloride → HCID 12988956, Verbindung

HRID 1070712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070712
[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([NH2:15])=O)[CH2:6][CH2:5]1)[CH2:2][CH3:3].O=P(Cl)(Cl)Cl>CN(C=O)C.O>[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]#[N:15])[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Komponenten

5

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 129889553-(1-Propyl-4-piperidinyl)benzamide

Produkt 1

HCID 12988956HCID 12988956, VerbindungAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-(1-propyl-piperidin-4-yl)-benzamide (350 mg) and POCl3 (326 μL) in dry DMF (6 ml) was heated at 80° C. for 3 h under an argon atmosphere. Evaporation of the solvent yielded a dark, oily residue, which was dissolved in water. The solution was basified and extracted with CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated. The oily residue was chromathographed on a silica column with MeOH:CH2Cl2 (1:19 (v/v)) as eluent. Collection of the fractions containing pure product and evaporation of the solvent afforded pure 3-(1-Propyl-piperidin-4-yl)-benzonitrile (127 mg). The amine was converted into the fumarate salt and recrystallized from ethanol/diethylether: m.p. 122° C.; MS m/z (relative intensity, 70 eV) 228 (M+, 2), 199 (42), 129 (26), 70 (bp) 56 (53).

Aufarbeitung

  1. customEvaporation of the solvent
  2. customyielded a dark, oily residue, which
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customCollection of the fractions
  8. additioncontaining pure
  9. customproduct and evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-bba457da25fc483d8a95d4e793ea2ecd
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903120B2

Notizen zur Reaktion

Wird geladen…