Acetic Acid → 1-Carbethoxy-4-dimethylamino-3-methylpiperidine

HRID 1814858Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1814858
C=O.N[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH:5]1[CH3:15].[C:16]([BH3-])#[N:17].[Na+].[C:20](O)(=O)C>CO>[C:10]([N:7]1[CH2:8][CH2:9][CH:4]([N:17]([CH3:16])[CH3:20])[CH:5]([CH3:15])[CH2:6]1)([O:12][CH2:13][CH3:14])=[O:11]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22278886Ethyl 4-amino-3-methylpiperidine-1-carboxylate

Produkt 1

HCID 222788651-Carbethoxy-4-dimethylamino-3-methylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Paraformaldehyde (5.1 g) was added to the stirred solution of 4-amino-1-carbethoxy-3-methylpiperidine (3.5 g, 18.8 mmol) in methanol (100 ml) at 0° C. and sodium cyanoborohydride (1.7 g, 27.0 mmol) was added to it. Then, acetic acid (1 ml) was added to the resulting mixture and stirring was continued for 96 hr at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water, acidified with conc. HCl (pH 3˜4) and extracted with ethyl acetate to remove impurities. The aqueous layer was basified with 1 M sodium hydroxide solution (pH˜10) and extracted with ethyl acetate. Ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to give 1-carbethoxy-4-dimethylamino-3-methylpiperidine. Yield 3.5 g (88%), C11H22N2O2, m/z 215 (M+1).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with water
  3. extractionextracted with ethyl acetate
  4. customto remove impurities
  5. extractionextracted with ethyl acetate
  6. extractionEthyl acetate extract
  7. dry with materialwas dried (Na2SO4)
  8. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-a3e30f50970f4993bafcd57770fde36e
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06878713B2

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