1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86646550, compound

HRID 1038762Notes

Reaction equation

HRID 1038762 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][N:15]3[CH2:20][C:21]([OH:23])=O)=[N:8][CH:9]=1)([O-:3])=[O:2].[O:24]1[C:28]2[CH:29]=[CH:30][C:31]([N:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH:34]3C)=[CH:32][C:27]=2[O:26][CH2:25]1.Cl.[CH2:41](N=C=NCCCN(C)C)C>C1COCC1.CN(C=O)C.[Cl-].[Na+].O>[O:26]1[C:27]2[CH:32]=[CH:41][C:30]([CH2:31][N:33]3[CH2:34][CH2:35][N:36]([C:21](=[O:23])[CH2:20][N:15]4[C:16]5[C:12](=[C:11]([O:10][C:7]6[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=6)[CH:19]=[CH:18][CH:17]=5)[CH:13]=[CH:14]4)[CH2:37][CH2:38]3)=[CH:29][C:28]=2[O:24][CH2:25]1

Participants

7

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 64938633HCID 64938633, compoundHCID 68495895HCID 68495895, compound

Product 1

HCID 86646550HCID 86646550, compoundYield 74.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

[4-(5-Nitropyridin-2-yloxy)indol-1-yl]acetic acid (0.210 g, 0.670 mmol) was dissolved in a mixture of THF (10 mL)-DMF (2 mL). To the solution were added 1-benzo[1,3]dioxol-5-yl-methylpiperazine (0.148 g, 0.670 mmol), then 1-ethyl-3-(3-di-methylaminopropyl)carbodiimide hydrochloride (0.129 g, 0.670 mmol), and the resulting solution was stirred for 3 hours at room temperature. Brine (50 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (30 mL). After the organic layer was washed with brine, then dried over anhydrous sodium sulfate, the solvent was evaporated. The obtained residue was recrystallized from ethyl acetate to yield 0.258 g of the title compound as pale brown powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (30 mL)
  2. washAfter the organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customThe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1bc859f298814d4fa5a21b9fde0aba6a
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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