Water → 4-Aminomethyl-1-diphenylmethylpiperidine

HRID 362884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362884
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[NH2:16][CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 540281161-Diphenylmethylpiperidine-4-carboxamide

Produkt 1

HCID 537860464-Aminomethyl-1-diphenylmethylpiperidineAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Step 2): 1-Diphenylmethylpiperidine-4-carboxamide (1.5 g, 5.1 mmol) was added dropwise to a suspension of LiAlH4 (0.4 g, 10.5 mmol) in THF (30 ml). The mixture was heated at 70° C. for 3 hours and then cooled. To the mixture, water (0.4 ml), 15% NaOH solution (0.4 ml) and water (1.2 ml) were added dropwise in order, and insoluble materials were filtered off. The filtrate was concentrated. The residue was purified by column chromatography on silica gel (10% methanol in dichloromethane) to give 4-aminomethyl-1-diphenylmethylpiperidine (57.0%) as colorless crystals: mp 80° C.

Aufarbeitung

  1. temperaturecooled
  2. filtrationwere filtered off
  3. concentrationThe filtrate was concentrated
  4. customThe residue was purified by column chromatography on silica gel (10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-179e11d834cb4439b1b0a49eec335370
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872115

Notizen zur Reaktion

Wird geladen…