Methylamine → 1198225-51-2

HRID 40792

Reaktionsgleichung

Reaktionsgleichung von HRID 40792
[C:1]1([C:7]2([C:10](O)=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[CH2:14][N:15]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CN>CN(C=O)C.CO>[CH3:14][NH:15][CH2:10][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][CH2:8]1

Komponenten

7

Edukt 4

HCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 802061-Phenylcyclopropanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 581687111198225-51-2Ausbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-Phenylcyclopropanecarboxylic acid (2.95 g) was dissolved in DMF (120 mL). To the solution, EDC.HCl (5.2 g), HOBt (3.2 g), and a solution of methylamine in methanol (40%, 1.94 mL) were added, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (50% ethyl acetate/hexane). An aliquot (1.1 g) of the obtained amide compound (2.9 g) was dissolved in THF (60 mL). To the solution, a solution of LAH in THF (2.4 M, 7.9 mL) was added dropwise at 0° C., and the mixture was heated to reflux at 80° C. for 12 hours. To the reaction mixture, water (4.0 mL) was gradually added dropwise at 0° C. The precipitate was removed by filtration and washed with THF (60 mL). Then, the combined filtrate was concentrated under reduced pressure to obtain the title compound (1.0 g) as a colorless oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (50% ethyl acetate/hexane)
  3. dissolutionAn aliquot (1.1 g) of the obtained amide compound (2.9 g) was dissolved in THF (60 mL)
  4. additionTo the solution, a solution of LAH in THF (2.4 M, 7.9 mL) was added dropwise at 0° C.
  5. temperaturethe mixture was heated
  6. temperatureto reflux at 80° C. for 12 hours
  7. additionTo the reaction mixture, water (4.0 mL) was gradually added dropwise at 0° C
  8. customThe precipitate was removed by filtration
  9. washwashed with THF (60 mL)
  10. concentrationThen, the combined filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f6bc5e03c5a04fc3b945c958532c1f0d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530490B2

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