Acetic acid methanol → HCID 178476567, Verbindung

HRID 2271531Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2271531
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([NH:11]C(=O)OCC2C=CC=CC=2)[CH2:7][CH2:6]1)[CH3:3].CO.[C:24]([OH:27])(=[O:26])[CH3:25]>[Pd]>[C:24]([OH:27])(=[O:26])[CH3:25].[C:24]([OH:27])(=[O:26])[CH3:25].[CH3:3][N:2]([CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[CH2:7][CH2:6]1)[CH3:1]

Komponenten

4

Edukt 2

HCID 10129899Acetic acid methanol2×HCID 66715796Carbamic acid, N-[trans-4-[(dimethylamino)methyl]cyclohexyl]-, phenylmethyl ester

Produkt 1

HCID 178476567HCID 178476567, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

To a flask containing Pd/C (1.5 g, Degussa type E101) was added methanol/acetic acid (100 mL, 3:1). Benzyl 4-((dimethylamino)methyl)cyclohexylcarbamate (15.8 g, 54 mmol) in methanol/acetic acid (300 mL, 3:1) was added. A balloon of H2 was added and the reaction stirred at rt for 6 h. The reaction was filtered through celite, the filtrate concentrated, and azeotroped with toluene. The thick oil was dried under vacuum to give desired product (17.9 g, crude) as a waxy solid. 1H NMR (300 MHz, MeOD) δ 3.11-2.98 (m, 1H), 2.78 (d, J=7.0 Hz, 2H), 2.69 (s, 6H), 2.07 (br d, J=13.9 Hz, 4H), 2.02-1.86 (m, 2H), 1.92 (s, 6H), 1.79-1.67 (m, 1H), 1.53-1.35 (m, 2H), 1.20-1.05 (m, 2H).

Aufarbeitung

  1. additionA balloon of H2 was added
  2. filtrationThe reaction was filtered through celite
  3. concentrationthe filtrate concentrated
  4. customazeotroped with toluene
  5. customThe thick oil was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-da74a59c1e6d4ab8b0fba14c9ca384b4
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120749B2

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