Trifluoroacetic acid → 2-(Piperidin-4-yl)acetonitrile

HRID 604312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604312
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]#[N:23])[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]#[N:23])[CH2:17][CH2:16]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 22248390tert-Butyl 4-(cyanomethyl)piperidine-1-carboxylate

Produkt 1

HCID 100119032-(Piperidin-4-yl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add trifluoroacetic acid (23 mL, 34.7 g, 304 mmol) to 4-cyanomethylpiperidine-1-carboxylic acid t-butyl ester (5.43 g, 24.21 mmol) in DCM (25 mL) and stir at room temperature for 18 hr. Remove the solvent in vacuo and dissolve in methanol (50 mL) and pour onto an SCX-2 column. Elute with 2 M ammonia in methanol and evaporate the eluent to give piperidin-4-ylacetonitrile as an oil which solidifies on standing (2.78 g, 92%). MS (m/z): 125.1 (M+1).

Aufarbeitung

  1. customRemove the solvent in vacuo
  2. dissolutiondissolve in methanol (50 mL)
  3. additionpour onto an SCX-2 column
  4. washElute with 2 M ammonia in methanol
  5. customevaporate the eluent

Quellen und Nachweise

ORD-Eintrag
ord-e35b087a342a4f1c8d6406b136ff8b5f
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910588B2

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