Hydrochloric Acid → HCID 19423990, compound

HRID 743227Notes

Reaction equation

HRID 743227 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH3:8][N:9]([CH3:31])[CH2:10][CH:11]([OH:30])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[ClH:32]>CC(C)=O.O1CCOCC1>[ClH:32].[C:4]([O:30][CH:11]([CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:10][N:9]([CH3:8])[CH3:31])(=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 107612473-Dimethylamino-1-[2-(4-phenylbutyl)phenoxy]-2-propanol

Product 1

HCID 19423990HCID 19423990, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 312751,4-DioxaneSolvent

Procedure

0.57 g of succinic anhydride was added to a solution of 1.79 g of 3-dimethylamino-1-[2-(4-phenylbutyl)phenoxy]-2-propanol [prepared as described in Example 1(b)] in 50 ml of acetone, and the resulting mixture was heated under reflux for 2 hours. At the end of this time, the reaction mixture was cooled, and 1.5 ml of a 4N solution of hydrogen chloride in dioxane were added, and the mixture was allowed to stand at room temperature. The crystals which precipitated were collected by filtration and dried in vacuo, to give 2.20 g (yield 93%) of the title compound as colorless crystals, melting at 123°-125° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAt the end of this time, the reaction mixture was cooled
  4. customto stand at room temperature
  5. customThe crystals which precipitated
  6. filtrationwere collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-bf99c4e7ee674c179990be667d99555e
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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