Formaldehyde → N-methyl-1-azabicyclo[2.2.2]octan-3-amine

HRID 542442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 542442
[CH2:1]([NH:8][CH:9]1[CH:14]2[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]2)[CH2:10]1)C1C=CC=CC=1.C=O.C([BH3-])#N.[Na+]>O>[CH3:1][NH:8][CH:9]1[CH:14]2[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]2)[CH2:10]1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 2615513-(Benzylamino)quinuclidineHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 19775384N-methyl-1-azabicyclo[2.2.2]octan-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a solution of 73.7 g of 3-benzylamino quinuclidine in water (≃300 to 400 ml) are added, while cooling to 5° C., 51 ml of a 40% aqueous formaldehyde solution. Then after the addition, the mixture is left for 30 minutes at 5° C., then 32 g of sodium cyanoborohydride are added within 1 to 2 hours. Then it is left at room temperature for 12 hours, extracted with ethyl acetate, the mixture obtained is dried on sodium (or magnesium) sulfate, filtered, the filtrate is evaporated and the residue is distilled (Boiling point [0.04 mm/Hg]=125° C.). Thus the expected product is obtained practically quantitatively.

Aufarbeitung

  1. additionThen after the addition
  2. waitThen it is left at room temperature for 12 hours
  3. extractionextracted with ethyl acetate
  4. customthe mixture obtained
  5. dry with materialis dried on sodium (or magnesium) sulfate
  6. filtrationfiltered
  7. customthe filtrate is evaporated
  8. distillationthe residue is distilled (Boiling point [0.04 mm/Hg]=125° C.)

Quellen und Nachweise

ORD-Eintrag
ord-d303726616f1422d9252d5a2a46172e2
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04657911

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