Dibutylamine → HCID 86682302, compound

HRID 1055197Notes

Reaction equation

HRID 1055197 reaction equation
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6]C)=O.[CH2:10]([NH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH3:13]>CO>[CH2:10]([N:14]([CH2:15][CH2:16][CH2:17][CH3:18])[C:4](=[O:6])[CH2:3][C:2](=[O:1])[CH2:8][CH3:9])[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 8148DibutylamineHCID 121699Methyl 3-oxovalerate

Product 1

HCID 86682302HCID 86682302, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

0.16 mol (20 ml) of methyl 3-oxovalerate (3-oxo-pentanoic acid methyl ester) and 0.415 mol (70 ml) of dibutylamine were stirred for 3 h at 130° C., where methanol formed was removed via a distillation bridge. Thereafter, excess dibutylamine was distilled on a rotary evaporator, the crude product taken up in 40 ml water and 90 ml of ethanol, with 3 ml 20% HCl adjusted to pH 3 and stirred for 1 h at 50° C. The mixture was again evaporated to dryness, dissolved again in 200 ml ethyl acetate and washed 3 times with 100 ml of water. The organic phase was dried over Na2SO4 and after filtration evaporated in a rotary evaporator to dryness. After drying, 31.8 g of the title compound were obtained.

Workup

  1. customwas removed via a distillation bridge
  2. distillationThereafter, excess dibutylamine was distilled on a rotary evaporator
  3. customThe mixture was again evaporated to dryness
  4. dissolutiondissolved again in 200 ml ethyl acetate
  5. washwashed 3 times with 100 ml of water
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationafter filtration
  8. customevaporated in a rotary evaporator to dryness
  9. customAfter drying

Sources & evidence

ORD record
ord-681d72c975554385867109a5e8cda5f0
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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