Reaction #1135820

ord-bfabc186a21b4ca28f4e67f89d44ad30

Reaction equation

CCCCCCCCCCCC(=O)OC
methyl laurate
CCCC(O)N(C)C
dimethylaminobutanol
CCCCCCCCCCCC(=O)OCCCN(C)C
3-dimethylaminopropyl laurate
Yield 67.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherA syringe was inserted
  2. 2
    Otherthrough the cap
  3. 3
    OtherNitrogen was bubbled at a rate sufficient
  4. 4
    workup.ADDITIONto mix the contents
  5. 5
    Otherset to 65° C
  6. 6
    Temperatureto cool
  7. 7
    OtherThe Novozym 435 was removed by filtration
  8. 8
    Otherto afford the product as a pale, yellow oil (9.2 g; 67% yield)
  9. 9
    Otherwithout further purification

Procedure

To a 50-mL conical bottom plastic vial was added methyl laurate (38.5 mmol), dimethylaminobutanol (46.2 mmol, 1.2 eq), and Novozym 435 (400 mg). A syringe was inserted through the cap and two additional holes were punched for gas to exit. Nitrogen was bubbled at a rate sufficient to mix the contents. The vial was placed in a heating block set to 65° C. The reaction was monitored by GC/MS to observe the disappearance of starting material. The reaction was complete after approximately 24 hours. The reaction mixture was allowed to cool. The Novozym 435 was removed by filtration to afford the product as a pale, yellow oil (9.2 g; 67% yield) without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09381147B2uspto-grants-2016_07