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

HRID 1080660Notes

Reaction equation

HRID 1080660 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>CCOCC.CO.C(OC(C)C)(C)C.CCOCC>[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)ethanolYield 101.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 21919906Ether isopropyl etherSolvent

Procedure

A solution of hydrogen chloride in ether is added to a solution of 3.4 g of 3-tetrahydropyranyloxyethyl-3-(3,4-dichlorophenyl)pyrrolidine in 20 ml of methanol until the pH is 1. The mixture is stirred for half an hour at room temperature and concentrated to dryness, the residue is taken up in water, rendered basic with a solution of sodium hydroxide and extracted with dichloromethane and the extract is washed with a saturated solution of NaCl, dried over Na2SO4 and evaporated to dryness to give an oil. This oil is taken up in 20 ml of an isopropyl ether/ether mixture (50/50 v/v). After stirring and filtration, the product is washed with ethyl ether and dried under vacuum over P2O5. 2.6 g of the expected product are isolated.

Workup

  1. concentrationconcentrated to dryness
  2. extractionextracted with dichloromethane
  3. washthe extract is washed with a saturated solution of NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customto give an oil
  7. stirringAfter stirring
  8. filtrationfiltration
  9. washthe product is washed with ethyl ether
  10. dry with materialdried under vacuum over P2O5

Sources & evidence

ORD record
ord-149e10b371054e009214d66c9ce01ce4
Source dataset
uspto-grants-1996_12
Patent number
US05583134

Reaction notes

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