Methyl Laurate → 3-Dimethylaminopropyl Laurate

HRID 1048638

Reaction equation

HRID 1048638 reaction equation
[C:1]([O:14][CH3:15])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:16][N:17]([CH:19](O)[CH2:20]CC)[CH3:18]>>[C:1]([O:14][CH2:15][CH2:20][CH2:19][N:17]([CH3:18])[CH3:16])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

3

Reactant 2

HCID 8139Methyl LaurateHCID 19917359Dimethylaminobutanol

Product 1

HCID 36130803-Dimethylaminopropyl LaurateYield 67%

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.

Workup

  1. customA syringe was inserted
  2. customthrough the cap
  3. customNitrogen was bubbled at a rate sufficient
  4. additionto mix the contents
  5. customset to 65° C
  6. temperatureto cool
  7. customThe Novozym 435 was removed by filtration
  8. customto afford the product as a pale, yellow oil (9.2 g; 67% yield)
  9. customwithout further purification

Sources & evidence

ORD record
ord-bfabc186a21b4ca28f4e67f89d44ad30
Source dataset
uspto-grants-2016_07
Patent number
US09381147B2

Linked notes

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