Sodium potassium tartrate tetrahydrate → 4-(Aminomethyl)-1-methylpiperidin-4-ol

HRID 905854

Reaktionsgleichung

Reaktionsgleichung von HRID 905854
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][NH2:16])([OH:14])[CH2:10][CH2:9]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>O1CCCC1>[NH2:16][CH2:15][C:11]1([OH:14])[CH2:12][CH2:13][N:8]([CH3:6])[CH2:9][CH2:10]1

Komponenten

5

Edukt 3

HCID 2724148Sodium potassium tartrate tetrahydrateHCID 21226445Aluminium lithium hydrideHCID 23396319tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 64842624-(Aminomethyl)-1-methylpiperidin-4-olAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A stirred mixture of 4-aminomethyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (529 mg, 2.3 mmol) in tetrahydrofuran (15 ml) was added slowly with lithium aluminum hydride (0.88 g, 23 mmol) while maintaining the temperature at 0˜5° C. Upon completion of the addition, the mixture was stirred at 80° C. in oil bath overnight. The mixture was added with potassium sodium tartrate tetrahydrate (6.3 g, 22.3 mmol) and stirred for 8 hours at room temperature. The mixture was filtered and washed with tetrahydrofuran (10 ml×3). The combined organic extracts were concentrated under reduced pressure to give 4-aminomethyl-1-methyl-piperidin-4-ol (245 mg, 74%) as a white oil which was used as such.

Aufarbeitung

  1. temperaturewhile maintaining the temperature at 0˜5° C
  2. additionUpon completion of the addition
  3. stirringstirred for 8 hours at room temperature
  4. filtrationThe mixture was filtered
  5. washwashed with tetrahydrofuran (10 ml×3)
  6. concentrationThe combined organic extracts were concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d1257b8f137c41d7bd69854f46ca03ce
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012966B2

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