p-Toluenesulfonic acid → HCID 178442213, Verbindung

HRID 485622

Reaktionsgleichung

Reaktionsgleichung von HRID 485622
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:13][CH2:12]2)=[CH:7][CH2:6]1)=[O:4].COC(C1CCC(=O)CC1)=O.C(C1CCNCC1)CCCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C1COCC1.[Pd]>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:13][CH2:12]2)[CH2:9][CH2:10]1)=[O:4]

Komponenten

8

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 226643Methyl 4-oxocyclohexanecarboxylateHCID 4070544-PentylpiperidineHCID 128095301-(4-Methoxycarbonylcyclohexen-1-yl)-4-pentylpiperidine

Produkt 1

HCID 178442213HCID 178442213, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 5 g of 1-(4-methoxycarbonylcyclohexen-1-yl)-4-pentylpiperidine (b.p. 171°/0.4 mm Hg, obtainable from methyl cyclohexanone-4-carboxylate and 4-pentylpiperidine in toluene in the presence of p-toluenesulfonic acid) in 50 ml of THF is hydrogenated under 2 bar of H2 using 0.5 g of 10% Pd-C; the catalyst is filtered off; and the filtrate is evaporated to dryness to give 1-(trans-4-methoxycarbonylcyclohexyl)4-pentylpiperidine, m.p. 5°, b.p. 177°/0.27 mbar.

Aufarbeitung

  1. filtrationthe catalyst is filtered off
  2. customand the filtrate is evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-1158fdd869af4b36a6f2bdf4433a6b30
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04537698

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