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

HRID 742628Notes

Reaction equation

HRID 742628 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. PREPARATION III: Scheme 1--Route B, m=2

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-47c41e678f674d199899a216ab461925
Source dataset
uspto-grants-1996_09
Patent number
US05554763

Reaction notes

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