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

HRID 982664

Reaktionsgleichung

Reaktionsgleichung von HRID 982664
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-cfa61e0512864ea2982376ff4693d72c
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06861433B2

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