1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 18372562, compound

HRID 1069509Notes

Reaction equation

HRID 1069509 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=O)[C:9]([OH:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[ClH:16].CN(C)[CH2:19][CH2:20][CH2:21][N:22]=C=NCC.O.ON1[C:34]2[CH:35]=[CH:36]C=C[C:33]=2N=N1>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([NH:22][CH2:21][C:20]2[CH:19]=[CH:33][C:34]([Cl:16])=[CH:35][CH:36]=2)=[O:14])[C:9]([OH:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 145347675-Chloro-8-hydroxyquinoline-7-carboxylic acid

Product 1

HCID 18372562HCID 18372562, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-8-hydroxyquinoline-7-carboxylic acid (0.335 g) of Preparation 3 and 4-chlorobonzylamine (0.219 g) in 20 mL DMF is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.305 g) and 1-hydroxybenzotriazole monohydrate (0.217 g). The mixture is stirred overnight. The solution is then poured into 30 mL ice-water. The resulting solid is collected and dried to yield 0.167 g of the title product as an off-white solid.

Workup

  1. customThe resulting solid is collected
  2. customdried

Sources & evidence

ORD record
ord-395805c8b878481a86d14defcecb7a0b
Source dataset
uspto-grants-2001_06
Patent number
US06252080B1

Reaction notes

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