Hydrochloric Acid → 2-[3-(3,4-Dichlorophenyl)piperidin-3-yl]ethanol

HRID 1489632Notes

Reaction equation

HRID 1489632 reaction equation
Cl.O1CCCCC1[O:8][CH2:9][CH2:10][C:11]1([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:16][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:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 211976913-(2-Tetrahydropyranyloxyethyl)-3-(3,4-dichlorophenyl)piperidine

Product 1

HCID 154604002-[3-(3,4-Dichlorophenyl)piperidin-3-yl]ethanolYield 106.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 21919906Ether isopropyl etherSolvent

Procedure

A saturated solution of hydrogen chloride in ether is added to a solution of 55 g of 3-(2-tetra-hydropyranyloxyethyl)-3-(3,4-dichlorophenyl)piperidine in 200 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 alkaline with a solution of NaOH and extracted with CH2Cl2 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 200 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 to give 45 g of the expected product. M.p.=22° C.

Workup

  1. concentrationconcentrated to dryness
  2. extractionextracted with CH2Cl2
  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-268c66df22d74c79a76d0adee1e6e00a
Source dataset
uspto-grants-1997_10
Patent number
US05679693

Reaction notes

Loading…