1,3-Dibenzyl-4-hydroxypiperidine → 4-Hydroxy-3-benzylpiperidine

HRID 396328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 396328
C([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1)C1C=CC=CC=1>CO.[H][H].[OH-].[Pd+2].[OH-]>[OH:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 1

HCID 230037131,3-Dibenzyl-4-hydroxypiperidine

Produkt 1

HCID 230036754-Hydroxy-3-benzylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittelHCID 178418361HCID 178418361, VerbindungLösungsmittel

Versuchsvorschrift

A mixture of 1,3-dibenzyl-4-hydroxypiperidine (1.7 g, 6.0 mmole) and 20% palladium hydroxide (0.3 g) in methanol (20 ml) was stirred in hydrogen atmosphere (1 atm.) for 12 hr at 35° C. Catalyst was filtered off, washed with methanol, filtrate was concentrated to dryness to give 4-hydroxy-3-benzylpiperidine as oil. Yield 1.0 g (91%), C12H17NO, m/z 192 (M+1) PMR (CDCl3): 1.66 (1H, m, H3), 1.94 (1H, m, H5), 2.26 (2H, m, H5, & OH, D2O exchangeable), 2.62 (1H, m, H2), 2.74 (1H, m, H6), 3.02 (1H, m, H2), 3.34 (1H, m, H6), 3.52 (1H, bs, NH, D2O exchangeable), 3.9 (1H, m, H4), 4.74 (2H, m, CH2-Ar), 7.28 (5H, m, ArH).

Aufarbeitung

  1. filtrationCatalyst was filtered off
  2. washwashed with methanol, filtrate
  3. concentrationwas concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-fbf4a62d9d524262b8f37191a528f44d
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608078B2

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