4-Chlorobenzylamine → HCID 21192514, compound

HRID 1067976Notes

Reaction equation

HRID 1067976 reaction equation
C([O:4][CH2:5][CH2:6][N:7]([CH2:25][CH3:26])[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[C:12]([C:19]([O:21]CC)=O)[C:11]2=[O:24])(=O)C.[Cl:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1>>[Cl:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH:33][C:19]([C:12]2[C:11](=[O:24])[C:10]3[C:15](=[CH:16][CH:17]=[C:8]([N:7]([CH2:25][CH3:26])[CH2:6][CH2:5][OH:4])[CH:9]=3)[N:14]([CH3:18])[CH:13]=2)=[O:21])=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 21192515HCID 21192515, compound

Product 1

HCID 21192514HCID 21192514, compound

Conditions

Temperature
190 °C

Procedure

To a flask containing ethyl 6-[[2-(acetyloxy)ethyl](ethyl)amino]-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylate from Preparation No. 16 (0.22 g) is added p-chlorobenzylamine (1.0 mL). The reaction is tightly capped and heated to 190° C. overnight. The reaction is cooled to room temperature. The residue is adsorbed onto silica and chromatographed on silica eluting with 4% to 8% methanol in dichloromethane. The product-containing fractions are evaporated to give 0.12 g of the title compound as a off-white solid.

Workup

  1. customfrom Preparation No
  2. customThe reaction is tightly capped
  3. temperatureThe reaction is cooled to room temperature
  4. customchromatographed on silica eluting with 4% to 8% methanol in dichloromethane
  5. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-6fa5849b716847779f980807b1dfb30c
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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