Dimethylamine → HCID 86682301, compound

HRID 1055195Notes

Reaction equation

HRID 1055195 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9].[CH3:12][NH:13][CH3:14].C(O)C>>[CH3:12][N:13]([CH3:14])[C:3](=[O:2])[CH2:4][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 702EthanolHCID 546075Methyl 3-oxoheptanoate

Product 1

HCID 86682301HCID 86682301, compound

Conditions

Temperature
100 °C

Procedure

0.632 mol (100 ml) methyl-3-oxoheptanoate (3-oxo-heptanoic acid methylester) and 227 ml 33% dimethylamine solution in ethanol (approx. 1.26 mol dimethylamine) was stirred for 4 hours at 110° C. in a pressure reactor. After cooling off, the solvents were distilled off on a rotavap, the raw product was taken up in 40 ml water, 30 ml 32% HCl and 40 ml ethanol and stirred for 24 hours at 100° C. The mixture was again concentrated to dryness by evaporation, taken up again in 300 ml acetic ester and filtrated, the solvents were then distilled off on the rotavap. 26 g of raw product was purified over 500 g silica gel 60 (mobile solvent: acetic ester:hexane 1:1, flow 50 ml/min, fraction size: 100 ml, product: fractions 20-35), the product was obtained as a mobile oil. 17.8 g of the title compound was obtained.

Workup

  1. temperatureAfter cooling off
  2. distillationthe solvents were distilled off on a rotavap
  3. concentrationThe mixture was again concentrated to dryness by evaporation
  4. filtrationfiltrated
  5. distillationthe solvents were then distilled off on the rotavap
  6. custom26 g of raw product was purified over 500 g silica gel 60 (mobile solvent: acetic ester:hexane 1:1, flow 50 ml/min, fraction size: 100 ml, product: fractions 20-35)
  7. customthe product was obtained as a mobile oil

Sources & evidence

ORD record
ord-136c28c071e14eac99a53093d352b3a2
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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