Ammonia → Piperidine-2-carboxamide

HRID 1437250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1437250
C(O[N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[C:15]([OH:17])=O)C1C=CC=CC=1.O[N:19]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.N>C(Cl)Cl.C(N(CC)CC)C>[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[C:15]([NH2:19])=[O:17]

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23090179N-benzyloxypiperidine-2-carboxylic acid

Produkt 1

HCID 140623Piperidine-2-carboxamideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

N-benzyloxypiperidine-2-carboxylic acid (2.0 g), 1-hydroxybenzotriazole (1.6 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.3 g) were dissolved in methylene chloride (20 mL). Concentrated aqueous ammonia (3 mL) and triethylamine (2 mL) were added to the resultant solution at room temperature, followed by stirring for 3 days. The reaction mixture was partitioned between water and methylene chloride. The organic layer was dried over magnesium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. 10% Palladium-carbon (1 g, 50% wet) was added to the residue in methanol (30 mL), and the resultant mixture was stirred in a hydrogen atmosphere for 20 hours. The catalyst was removed by filtration. The solvent was evaporated under reduced pressure, and the thus-obtained oily product was dried, to thereby give the title compound as a solid (970 mg, quantitative amount).

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and methylene chloride
  2. dry with materialThe organic layer was dried over magnesium sulfate anhydrate
  3. filtrationfollowed by filtration
  4. customThe solvent was evaporated under reduced pressure
  5. addition10% Palladium-carbon (1 g, 50% wet) was added to the residue in methanol (30 mL)
  6. stirringthe resultant mixture was stirred in a hydrogen atmosphere for 20 hours
  7. customThe catalyst was removed by filtration
  8. customThe solvent was evaporated under reduced pressure
  9. customthe thus-obtained oily product was dried

Quellen und Nachweise

ORD-Eintrag
ord-16d6bc878bb74cf09047527f62acc296
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622471B2

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