Ethyl Acetate → Hydrochloric Acid

HRID 1249200Notes

Reaction equation

HRID 1249200 reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=O)[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2].[CH3:17][O:18][CH:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[CH2:20][NH2:21].C(OCC)(=O)C>C1(C)C=CC=CC=1>[ClH:28].[ClH:28].[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:21][CH2:20][CH:19]([O:18][CH3:17])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 13851156Methyl 2-(4-(2-oxopropyl)phenoxy)acetateHCID 20225281HCID 20225281, compound

Product 2

HCID 313Hydrochloric AcidHCID 20225212HCID 20225212, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(4-carbomethoxymethoxyphenyl)propan-2-one (2.80 g) and 2-methoxy-2-(3-chlorophenyl)ethanamine (2.58 g) in dry toluene (200 ml) were boiled under reflux for 2 hours in an apparatus incorporating a water trap. The solution was cooled and the solvent removed under reduced pressure. The residue dissolved in methanol (100 ml) was hydrogenated in the presence of platinum (from platinum oxide, 50 mg) until hydrogen uptake ceased. The solution was filtered through diatomaceous earth, and the solvent removed under reduced pressure. Chromatography of the residue on silica-gel in 3% methanol-dichloromethane gave an oil. Treatment of this oil with an ethereal solution of hydrogen chloride gave N-[2-(4-carbomethoxymethoxyphenyl)-1-methylethyl]-2-methoxy-2-(3-chlorophenyl)ethanamine hydrochloride, mp 148°-50° C. (ethyl acetate), as an 85:15 mixture of diastereoisomers.

Workup

  1. temperatureunder reflux for 2 hours in an apparatus
  2. temperatureThe solution was cooled
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe residue dissolved in methanol (100 ml)
  5. filtrationThe solution was filtered through diatomaceous earth
  6. customthe solvent removed under reduced pressure
  7. customChromatography of the residue on silica-gel in 3% methanol-dichloromethane gave an oil

Sources & evidence

ORD record
ord-ad4bf6c1348a44908e41bef67887b49c
Source dataset
uspto-grants-1986_12
Patent number
US04629737

Reaction notes

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