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

HRID 982664

Reaction equation

HRID 982664 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 5273472trans-CinnamamideYield 51%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cfa61e0512864ea2982376ff4693d72c
Source dataset
uspto-grants-2005_03
Patent number
US06861433B2

Linked notes

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