2-Propenoic acid, 3-phenyl- → HCID 54023334, compound

HRID 1596222Notes

Reaction equation

HRID 1596222 reaction equation
Br.[N:2]1([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:18](O)(=[O:27])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C.C(N(CC)CC)C>[C:18]([N:5]1[CH2:4][CH2:3][N:2]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:7][CH2:6]1)(=[O:27])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

9

Reactant 4

HCID 87842-Propenoic acid, 3-phenyl-HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21701628HCID 21701628, compound

Product 1

HCID 54023334HCID 54023334, compoundYield 40.2%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of N-piperazinyl-p-fluorobenzamide hydrobromide (300 mg), cinnamic acid (161 mg), and 1-hydroxybenzotriazole (173 mg) in N,N-dimethylformamide (6 ml) was added N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (246 mg) and triethylamine (0.28 ml) at 5° C. The mixture was stirred at 5° C. for 1 hour, and then poured into ethyl acetate and brine. The organic layer was separated, dried over magnesium sulfate, and concentrated. The residue was crystallized from ethyl acetate-diethyl ether to give N-(4-cinnamoyl-1-piperazinyl)-p-fluorobenzamide (0.14 g).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was crystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-67a6f54f9b5941a1a06bb0e66dcc7994
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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