Glycine → Glycine, N-cyclohexyl-

HRID 1899751

Reaktionsgleichung

Reaktionsgleichung von HRID 1899751
[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 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 rotavapped 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 weighed 252.5 grams; it was stirred into excess either whereby a white solid precipitate out. The solid was filtered and washed with ether. The filtrate was yellow and the washing was light yellow. The solid was dried in the hood overnight. The solid was redissolved in a very small amount of acetic acid and recrystallized by adding 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; O:20.41.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-b89f3e4c51bb47c488c00cd93dac60fb
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05573746

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