4-{4-[2-({(2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl}amino)ethyl]phenoxy}-N-octyl-1-piperidinecarboxamide → 4-[4-(2-{[(2S)-2-Hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl)phenoxy}-N-octyl-1-piperidinecarboxamide

HRID 1281548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1281548
C([O:8][C:9]1[CH:46]=[CH:45][C:12]([O:13][CH2:14][C@@H:15]([OH:44])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:43]=[CH:42][C:23]([O:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]([NH:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:32])[CH2:27][CH2:26]3)=[CH:22][CH:21]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C>[OH:44][C@H:15]([CH2:14][O:13][C:12]1[CH:45]=[CH:46][C:9]([OH:8])=[CH:10][CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH:25]2[CH2:26][CH2:27][N:28]([C:31]([NH:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:32])[CH2:29][CH2:30]2)=[CH:42][CH:43]=1

Komponenten

4

Edukt 1

HCID 699867334-{4-[2-({(2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl}amino)ethyl]phenoxy}-N-octyl-1-piperidinecarboxamide

Produkt 1

HCID 101872354-[4-(2-{[(2S)-2-Hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl)phenoxy}-N-octyl-1-piperidinecarboxamideAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 4-{4-[2-({(2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl}amino)ethyl]phenoxy}-N-octyl-1-piperidinecarboxamide (0.2 g, 0.32 mmol), and 10% palladium on carbon (0.3 g) in ethanol (5 mL) was stirred under atmospheric hydrogen for 11 hours. The catalyst was filtered and the filtrate evaporated in vacuo to a residue (0.1 g). The residue was treated with a solution of anhydrous hydrogen chloride in methanol followed by ethyl acetate and diethyl ether. The precipitate was filtered and after drying in vacuo overnight yielded the title compound (0.1 g, 0.17 mmol).

Aufarbeitung

  1. filtrationThe catalyst was filtered
  2. customthe filtrate evaporated in vacuo to a residue (0.1 g)
  3. additionThe residue was treated with a solution of anhydrous hydrogen chloride in methanol
  4. filtrationThe precipitate was filtered
  5. customafter drying in vacuo overnight

Quellen und Nachweise

ORD-Eintrag
ord-b82cabeb0d76449ca9e87f41f585b482
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451814B1

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