Hydrochloric Acid → HCID 15389032, compound

HRID 743188Notes

Reaction equation

HRID 743188 reaction equation
[OH-:1].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:28]=[CH:27][CH:26]=[CH:25][C:16]=1[O:17][CH2:18][CH:19]([OH:24])[CH2:20][N:21]([CH3:23])[CH3:22])#[N:4].Cl>C(O)C.C(Cl)Cl>[CH3:23][N:21]([CH3:22])[CH2:20][CH:19]([OH:24])[CH2:18][O:17][C:16]1[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=1[CH2:14][CH2:13][CH2:12][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]([NH2:4])=[O:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15389031HCID 15389031, compound

Product 1

HCID 15389032HCID 15389032, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

2 ml of an aqueous solution containing 1 g of sodium hydroxide were added to a solution of 430 mg of 1-{2-[4-(2-cyanophenyl)butyl]phenoxy}-3-dimethylamino-2-propanol [prepared as described in Example 9(b)] in 5 ml of ethanol, and the resulting mixture was heated under reflux for 15 hours. At the end of this time, the reaction mixture was neutralized by the addition of aqueous hydrochloric acid, after which it was concentrated by evaporation under reduced pressure. The resulting residue was mixed with ethanol, and insoluble materials were filtered off. The filtrate was concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 3:1 by volume mixture of methylene chloride and methanol as the eluent, to give a colorless oily material, which was dissolved in a small amount of methylene chloride and then allowed to stand at room temperature. The crystals which precipitated were collected by filtration and dried in vacuo, to give 238 mg (yield 62%) of the title compound as colorless crystals, melting at 149°-151° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 15 hours
  3. concentrationafter which it was concentrated by evaporation under reduced pressure
  4. additionThe resulting residue was mixed with ethanol, and insoluble materials
  5. filtrationwere filtered off
  6. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  7. customthe residue was purified by column chromatography through silica gel
  8. additionby volume mixture of methylene chloride and methanol as the eluent
  9. customto give a colorless oily material, which
  10. customto stand at room temperature
  11. customThe crystals which precipitated
  12. filtrationwere collected by filtration
  13. customdried in vacuo

Sources & evidence

ORD record
ord-e18549daa2d943ab9f93867a002cf575
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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