Water → 1-(2-Phenylethyl)-4-methyl-4-hydroxymethyl-piperidine

HRID 1708050Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1708050
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][C:18]([CH3:26])([C:21](OCC)=[O:22])[CH2:17][CH2:16]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>C1COCC1>[C:7]1([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][C:18]([CH3:26])([CH2:21][OH:22])[CH2:17][CH2:16]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18997143HCID 18997143, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 189971411-(2-Phenylethyl)-4-methyl-4-hydroxymethyl-piperidineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 0.51 g (13.4 mmol) of lithium aluminum hydride in 20 mL of THF under nitrogen was added dropwise a solution of 3.70 g (13.4 mmol) of 1-(2phenylethyl)-4-methyl-4-carboethoxypiperidine in 15 mL of THF. The solution was heated at reflux for 3 hours. To the cooled reaction mixture (ice bath) was slowly added 0.5 mL of water, followed by 0.5 mL of 15% sodium hydroxide followed by 1.5 mL of water. The precipitated lithium salts were removed by filtration. The filtrate was evaporated to dryness. The residue was reconstituted in methylene chloride, washed with a small amount of water, dried and evaporated to afford 2.97 g of 1-(2-phenylethyl)-4-methyl-4-hydroxymethyl-piperidine as a yellow oil. NMR (CDCl3) δ7.16-7.23 (m, 5H); 3.40 (s, 2H); 2.79-2.87 (m, 2H); 2.57-2.71 (m, 4H); 2.31-2.42 (m, 2H); 1.57-1.63 (m, 5H); 0.97 (s, 3H).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 hours
  3. customTo the cooled reaction mixture (ice bath)
  4. customThe precipitated lithium salts were removed by filtration
  5. customThe filtrate was evaporated to dryness
  6. washwashed with a small amount of water
  7. customdried
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c7ac832383fc44d68a965bb91c289bc3
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05356906

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