Butylamine → HCID 86682308, compound

HRID 1055236Notes

Reaction equation

HRID 1055236 reaction equation
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6]C)=O.[CH2:12]([NH2:16])[CH2:13][CH2:14][CH3:15]>>[CH2:12]([NH:16][C:4](=[O:6])[CH2:3][C:2](=[O:1])[CH2:8][CH2:9][CH2:10][CH3:11])[CH2:13][CH2:14][CH3:15]

Participants

3

Reactant 2

HCID 8007ButylamineHCID 546075Methyl 3-oxoheptanoate

Product 1

HCID 86682308HCID 86682308, compoundYield 20.1%

Procedure

0.9 mol (150 ml) of methyl 3-oxoheptanoate and 2.7 mol (270 ml) butylamine, were stirred 5 h at 100° C. in the pressure vessel. Thereafter, excess butylamine was distilled off on a rotary evaporator, the crude product was taken up in water/ethanol, and adjusted with concentrated HCl to pH 3. The mixture was again evaporated to dryness, taken up again in ethyl acetate and filtered. The filtrate was washed with 1 M HCl and water. The organic phase was dried over Na2SO4 and after filtration evaporated in a rotary evaporator to dryness. The crude product was dissolved in 100 ml diethyl ether and crystallized at 5° C. The product was filtered off and dried. There were obtained 36.0 g of the title compound.

Workup

  1. distillationThereafter, excess butylamine was distilled off on a rotary evaporator
  2. customThe mixture was again evaporated to dryness
  3. filtrationfiltered
  4. washThe filtrate was washed with 1 M HCl and water
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationafter filtration
  7. customevaporated in a rotary evaporator to dryness
  8. dissolutionThe crude product was dissolved in 100 ml diethyl ether
  9. customcrystallized at 5° C
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-41d19e9e92074ccda923af82be018bc1
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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