Hydrochloric Acid → HCID 15290691, compound

HRID 2257903Notes

Reaction equation

HRID 2257903 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][S:17]([N:20]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:40])[CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH:26]([O:29]COC)[CH2:25][CH2:24]3)(=[O:19])=[O:18])[CH:8]=2)[N:3]=1.C[OH:42].Cl.[OH-].[K+]>C(O)(=O)C>[Cl:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][N:20]([CH2:21][CH2:22][N:23]1[CH2:24][CH2:25][CH:26]([OH:29])[CH2:27][CH2:28]1)[S:17]([CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:42])[CH:11]=[CH:10]2)(=[O:18])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 22923719HCID 22923719, compound

Product 1

HCID 15290691HCID 15290691, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.63 g of 2-chloro-6-[4-{N-(2-chlorobenzyl)-N-[2-(4-methoxymethoxy-1-piperidinyl)-ethyl]aminosulfonyl}butoxy]quinoline dissolved in 50 ml of acetic acid was refluxed for 3.5 hours. The solvent was removed by distillation under reduced pressure to obtain crude 6-[4-{N-(2-chlorobenzyl)-N-[2-(4-methoxymethoxy-1-piperidinyl)ethyl]aminosulfonyl}-butoxy]carbostyril. To the substance were added 10 ml of methanol and 10 ml of a 5% aqueous hydrochloric acid solution. The mixture was stirred at room temperature for 1 day and then made alkaline with an aqueous potassium hydroxide solution, followed by extraction with ethyl acetate. The extract was washed with water and dried with magnesium sulfate. The solvent was removed by distillation. The resulting residue was purified by silica gel column chromatography (eluant: 10% methanol/dichloromethane) to obtain 1.4 g of 6-[4-{N-(2-chlorobenzyl)-N-[2-(4-hydroxy-l-piperidinyl)ethyl]-aminosulfonyl}butoxy]carbostyril.

Workup

  1. temperaturewas refluxed for 3.5 hours
  2. customThe solvent was removed by distillation under reduced pressure
  3. customto obtain crude 6-[4-{N-(2-chlorobenzyl)-N-[2-(4-methoxymethoxy-1-piperidinyl)ethyl]aminosulfonyl}-butoxy]carbostyril
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried with magnesium sulfate
  7. customThe solvent was removed by distillation
  8. customThe resulting residue was purified by silica gel column chromatography (eluant: 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-ba64f89916ed4473b24c1714c1fe5d04
Source dataset
uspto-grants-1997_08
Patent number
US05658926

Reaction notes

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