1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → trans-Cinnamamide

HRID 25271

Reaktionsgleichung

Reaktionsgleichung von HRID 25271
Cl.CN(C)[CH2:4][CH2:5][CH2:6][N:7]=C=NCC.[OH2:13].ON1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2N=N1>N1C=CC=CC=1>[CH:18]1[CH:23]=[CH:22][C:21](/[CH:4]=[CH:5]/[C:6]([NH2:7])=[O:13])=[CH:20][CH:19]=1

Komponenten

4

Edukt 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 5273472trans-CinnamamideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

The amine bis-hydrochloride (from Step 4) (68.2 mg, 0.19 mmol), the lithium carboxylate prepared in Step 3, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (72.8 mg, 0.38 mmol) and 1-hydroxybenzotriazole hydrate (30.8 mg, 0.23 mmol) are dissolved in pyridine (2 ml) and stirred at room temperature for 72 hours. The reaction mixture is concentrated. The residue is dissolved in CH2Cl2 (40 ml) and washed with H2O (20 ml), brine (20 ml), dried (MgSO4), filtered and concentrated. The residue is dissolved in CH3OH/CH2Cl2, absorbed onto silica gel and is purified on a Biotage 12M column with SIM using 2% CH3OH (saturated with NH3) in CH2Cl2 as the eluent to afford 56.2 mg (0.096 mmol, 51%) of the desired cinnamide. 1H-NMR (DMSO) δ: 8.66, 8.48, 8.02, 7.64, 7.49, 7.40, 7.35, 6.70, 4.86, 4.22, 3.84, 3.60.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated
  2. dissolutionThe residue is dissolved in CH2Cl2 (40 ml)
  3. washwashed with H2O (20 ml), brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue is dissolved in CH3OH/CH2Cl2
  8. customabsorbed onto silica gel
  9. customis purified on a Biotage 12M column with SIM

Quellen und Nachweise

ORD-Eintrag
ord-4ca0cc3d4bf04c8fb8b805fcd65a7aa4
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858635B2

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