1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 57499605, compound

HRID 655668Notes

Reaction equation

HRID 655668 reaction equation
O.N.Cl.C[N:5](C)CCCN=C=NCC.[S:15]1[CH:19]=[CH:18][C:17]2[C:20]([N:24]3[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32][O:33][CH:34]4[CH2:39][CH2:38][CH:37]([C:40](O)=[O:41])[CH2:36][CH2:35]4)[CH2:26][CH2:25]3)=[CH:21][CH:22]=[CH:23][C:16]1=2>CN(C)C1C=CN=CC=1.ClCCl>[S:15]1[CH:19]=[CH:18][C:17]2[C:20]([N:24]3[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32][O:33][CH:34]4[CH2:39][CH2:38][CH:37]([C:40]([NH2:5])=[O:41])[CH2:36][CH2:35]4)[CH2:26][CH2:25]3)=[CH:21][CH:22]=[CH:23][C:16]1=2

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12896473Azane;hydrateHCID 57499606HCID 57499606, compound

Product 1

HCID 57499605HCID 57499605, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Ammonia water (28%, 0.5 ml), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (WSC)(0.36 g, 1.9 mmol) and 4-dimethylaminopyridine (DMAP) (0.05 g, 0.4 mmol) were added to a dichloromethane solution (10 ml) of 4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-cyclohexanecarboxylic acid (0.5 g, 1.2 mmol) and the mixture was stirred at room temperature for 19 hours. To the reaction solution, dichloromethane was added and the mixture was washed with water. The organic layer was dried over anhydrous magnesium sulfate and thereafter concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=3:1→0:1). The purified product was concentrated under reduced pressure and the residue was recrystallized from a solvent mixture of ethyl acetate-diisopropylether to obtain 4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)-propoxy]-cyclohexanecarboxylic acid amide (0.1 g, 22% yield), as white powder.

Workup

  1. washthe mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=3:1→0:1)
  5. concentrationThe purified product was concentrated under reduced pressure
  6. customthe residue was recrystallized from a solvent mixture of ethyl acetate-diisopropylether

Sources & evidence

ORD record
ord-08a89e8cbbe841d280833a50cf9601db
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

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