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

HRID 988623Notes

Reaction equation

HRID 988623 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-ff75b5e4caa54dfea5a4404d505f007f
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

Loading…