Triethylamine → HCID 57164571, compound

HRID 344547Notes

Reaction equation

HRID 344547 reaction equation
C(N(CC)CC)C.I.CS[C:11]1[NH:12][CH2:13][CH2:14][N:15]=1.[NH2:16][C:17]1[C:38]([Cl:39])=[CH:37][C:20]([C:21]([NH:23][CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])[CH2:27][CH2:26]2)=[O:22])=[C:19]([O:40][CH3:41])[CH:18]=1.[OH-].[Na+]>CO>[NH2:16][C:17]1[C:38]([Cl:39])=[CH:37][C:20]([C:21]([NH:23][CH2:24][CH:25]2[CH2:26][CH2:27][N:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:11]3[NH:12][CH2:13][CH2:14][N:15]=3)[CH2:29][CH2:30]2)=[O:22])=[C:19]([O:40][CH3:41])[CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 122212281H-Imidazole, 4,5-dihydro-2-(methylthio)-, hydriodide (1:1)HCID 540083634-Amino-N-(1-(5-aminopentyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

Product 1

HCID 57164571HCID 57164571, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (0.59 g) and 2-methylthio-2-imidazoline hydroiodide (1.4 g) were added to a solution of 4-amino-N-((1-(5-aminopentyl)-piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamide (1.5 g) in methanol (20 ml), and the mixture was stirred at refluxing temperature for 4 hr. A 10% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with chloroform. The extract was washed with brine and dried. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 0.84 g of 4-amino-5-chloro-N-((1-(5-(imidazolin-2-ylamino)pentyl)piperidin-4-yl)methyl)-2-methoxybenzamide.

Workup

  1. temperatureat refluxing temperature for 4 hr
  2. extractionthe mixture was extracted with chloroform
  3. washThe extract was washed with brine
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b6afc58dd3894b10b2218bccb9eceec7
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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