Glycine → Glycine, N-cyclohexyl-

HRID 849436

Reaktionsgleichung

Reaktionsgleichung von HRID 849436
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[C:6]1(=O)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[H][H]>[Pd].C(O)(=O)C>[CH:6]1([NH:1][CH2:2][C:3]([OH:5])=[O:4])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Komponenten

6

Edukt 3

HCID 750GlycineHCID 7967CyclohexanoneHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 42810Glycine, N-cyclohexyl-Ausbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Similar equipment and procedure as described in Example 1 were employed. 75.5 grams glycine (1.01 moles, Aldrich, 99+%), 118.4 grams cyclohexanone (1.21 moles, Aldrich 99.8%), 300 ml glacial acetic acid and 11.2 grams of Pd (5%)/C were used. The reaction was carried out in a 600 ml Parr reactor under 1000 psig (7000 kPa) hydrogen pressure at 75° C. No noticeable hydrogen uptake was noticed after 1.5 days, and the reaction was carried out for 4.5 days. The reactor was opened after cooling to room temperature. The solid catalyst was filtered by suction. The filtrate was evaporated to remove the acetic acid and the excess cyclohexanone. A viscous crude product (brown) remained which started to crystallize upon cooling to room temperature. The crude product was stirred into excess ether whereby a white solid precipitated out. The solid was filtered, washed with ether and dried. The solid was redissolved in a very small amount of acetic acid and recrystallized by adding an appropriate amount of ether. 144.5 grams of white crystals were recovered (91% yield based on glycine). Elemental analysis:calculated: C:61.12; H:9.62; N:8.91; 0:20.36; found:C:60.96; H:9.75; N:8.88; 0:20.41.

Aufarbeitung

  1. filtrationThe solid catalyst was filtered by suction
  2. customThe filtrate was evaporated
  3. customto remove the acetic acid
  4. customto crystallize
  5. temperatureupon cooling to room temperature
  6. customprecipitated out
  7. filtrationThe solid was filtered
  8. washwashed with ether
  9. customdried
  10. dissolutionThe solid was redissolved in a very small amount of acetic acid
  11. customrecrystallized
  12. additionby adding an appropriate amount of ether
  13. custom144.5 grams of white crystals were recovered (91% yield based on glycine)

Quellen und Nachweise

ORD-Eintrag
ord-812d32df2c1748b7be5316f9574ca740
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06013239

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