Hydrochloric Acid → 2-(3-(3,4-Dichlorophenyl)pyrrolidin-3-yl)ethanol

HRID 975081Notes

Reaction equation

HRID 975081 reaction equation
Cl.O1CCCCC1[O:8][CH2:9][CH2:10][C:11]1([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:15][CH2:14][NH:13][CH2:12]1>C(OCC)C.CO.C(OC(C)C)(C)C.C(OCC)C>[OH:8][CH2:9][CH2:10][C:11]1([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:15][CH2:14][NH:13][CH2:12]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 211976873-Tetrahydropyranyloxyethyl-3-(3,4-dichlorophenyl)pyrrolidine

Product 1

HCID 184644272-(3-(3,4-Dichlorophenyl)pyrrolidin-3-yl)ethanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 21919906Ether isopropyl etherSolvent

Procedure

A saturated solution of hydrogen chloride in diethyl ether is added to a solution of 55 grams of 3-(2-tetrahydropyranyloxyethyl)-3-(3,4dichlorophenyl)pyrrolidine in 200 ml of methanol until the pH is 1.0. The mixture is stirred for about thirty minutes at room temperature and concentrated to dryness. The residue is then taken up in water, rendered alkaline with a solution of sodium hydroxide and extracted with methylene chloride. The extract is then washed with a saturated solution of sodium chloride, dried over sodium sulfate, and evaporated to dryness to give an oil. The oil is taken up in 200 ml of an isopropyl ether/diethyl ether mixture (50/50).After stirring and filtration, the desired intermediate is washed with ethyl ether and dried over phosphorous pentoxide.

Workup

  1. concentrationconcentrated to dryness
  2. extractionextracted with methylene chloride
  3. washThe extract is then washed with a saturated solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customto give an oil
  7. filtrationfiltration
  8. washthe desired intermediate is washed with ethyl ether
  9. dry with materialdried over phosphorous pentoxide

Sources & evidence

ORD record
ord-17bebdbafbac4f5fa45ed76e98feab76
Source dataset
uspto-grants-1997_03
Patent number
US05607947

Reaction notes

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