Dichloromethane → 1-(4-Ethylcyclohexyl)-3-(1-isobutyrylpiperidin-4-yl)urea

HRID 574688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 574688
F[C:2](F)(F)[C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:26])[CH:22]([CH3:25])[CH2:23]C)[CH2:17][CH2:16]1.[CH2:27](Cl)Cl>>[CH2:2]([CH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:26])[CH:22]([CH3:25])[CH3:23])[CH2:17][CH2:16]2)=[O:11])[CH2:5][CH2:4]1)[CH3:27]

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 167829341-(4-Amino-1-piperidinyl)-2-methyl-1-butanone

Produkt 1

HCID 716780091-(4-Ethylcyclohexyl)-3-(1-isobutyrylpiperidin-4-yl)ureaAusbeute 42 %

Versuchsvorschrift

4-(Trifluoromethyl)phenylisocyanate (100 mg, 0.65 mmol) and 1-(4-aminopiperidin-1-yl)-2-methylbutan-1-one (111 mg, 0.53 mmol) was dissolved in CH2Cl2 (100 mL) and stirred for 12 h. The reaction was quenched by addition of water. The organic layer was isolated and the aqueous layer was extracted with EtOAc for 4 times. The combined organic layer was concentrated under vacuo and was further purified by flash chromatography (EtOAc:Hex/1:1) yielding final product (89 mg, 2.76 mmol, 42%). H-NMR (DMSO-d6) ∂ 0.83 (t, J=8 Hz, 3H), 0.91 (m, 1H), 0.97 (m, 7H), 1.03 (m, 3H), 1.16 (m, 4H), 1.69 (m, 3H), 1.78 (m, 3H), 2.72 (t, J=12 Hz, 1H), 2.85 (m, 1H), 3.10 (t, J=12 Hz, 1H), 3.24 (m, 1H), 3.57 (m, 1H), 3.79 (d, J=13 Hz, 1H), 4.14 (d, J=13 Hz, 1H), 5.56 (d, J=7.5 Hz, 1H), 5.70 (d, J=7.5 Hz, 1H).

Aufarbeitung

  1. customThe reaction was quenched by addition of water
  2. customThe organic layer was isolated
  3. extractionthe aqueous layer was extracted with EtOAc for 4 times
  4. concentrationThe combined organic layer was concentrated under vacuo
  5. customwas further purified by flash chromatography (EtOAc:Hex/1:1)

Quellen und Nachweise

ORD-Eintrag
ord-b897d4b10249411582059d8ed0368668
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034903B2

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