1,2-Dichloroethane → HCID 57733287, Verbindung

HRID 1920752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1920752
[C:1]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12]([OH:14])=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[C:1]([N:5]1[CH2:6][CH2:7][CH:8]([CH2:11][C:12]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])[CH2:9][CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 19439052HCID 19439052, Verbindung

Produkt 1

HCID 57733287HCID 57733287, VerbindungAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of (1-tert-butyl-piperidin-4-yl)-acetic acid (672 mg, 3.37 mmol), aniline (0.32 ml, 3.5 mmol), and HOBt (568 mg, 4.2 mmol) in DMF (20 ml), EDC (805 mg, 4.2 mmol) was added. It was stirred at r.t. for 2 hours and partitioned between water (200 ml) and ethyl acetate (200 ml). The organic phase was washed with 0.5 N aq. NaOH (2×50 ml) and brine (3×50 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on (SiO2, gradient heptane-ethyl acetate) to give 250 mg of the title compound. 1H NMR (500 MHz, DMSO-d6): 1.07 (s, 9H), 1.32 (br. m, 2H), 1.81 (br. d, 2H), 1.89 (m, 1H), 2.11 (br. t, 2H), 2.25 (d, 2H), 3.03 (br. d, 2H), 7.1 (t, 1H), 7.24 (br., 1H), 7.31 (t, 2H), 7.52 (d, 2H).

Aufarbeitung

  1. additionwas added
  2. custompartitioned between water (200 ml) and ethyl acetate (200 ml)
  3. washThe organic phase was washed with 0.5 N aq. NaOH (2×50 ml) and brine (3×50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on (SiO2, gradient heptane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c410419490784cfeb0be7049ed5e9ec5
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173639B2

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