1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 21906521, compound

HRID 1247055Notes

Reaction equation

HRID 1247055 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([NH:16][C:17]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:18]=2[C:19](O)=[O:20])=[O:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[O:15][C:19](=[O:20])[C:18]3[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21906205HCID 21906205, compound

Product 1

HCID 21906521HCID 21906521, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 2-[(4-Boc-piperazin-1-ylcarbonyl)amino]-5-chlorobenzoic acid (1.6 g, 4.17 mmol) in DMF (30 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.4 g, 12.51 mmol). After 30 min, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The layers were separated and the organic phase was washed consecutively with 1 M citric acid, brine, sat. aq sodium bicarbonate, and brine, then dried with MgSO4, filtered and concentrated in vacuo. The residue was then suspended in diethyl ether, sonicated, filtered and dried in vacuo to give 0.86 g (58%) of the title compound as a white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic phase was washed consecutively with 1 M citric acid, brine, sat. aq sodium bicarbonate, and brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customsonicated
  9. filtrationfiltered
  10. customdried in vacuo

Sources & evidence

ORD record
ord-ddacdb56457746129707fff207379386
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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