Hydrochloric Acid → Trans-4-(2-chlorophenoxy)-1-ethyl-3-pyrrolidinol Hydrochloride

HRID 1262609Notes

Reaction equation

HRID 1262609 reaction equation
[CH2:1]([N:3]1[CH2:7][CH:6]2[O:8][CH:5]2[CH2:4]1)[CH3:2].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16].Cl>Cl.C(Cl)Cl>[ClH:9].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][C@@H:6]1[CH2:7][N:3]([CH2:1][CH3:2])[CH2:4][C@H:5]1[OH:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 72452-ChlorophenolHCID 13320194N-ethyl-3,4-epoxypyrrolidine

Product 1

HCID 70454118Trans-4-(2-chlorophenoxy)-1-ethyl-3-pyrrolidinol Hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 17.0 g. (0.15 mole) of 1-ethyl-3,4-epoxypyrrolidine, 20.5 g. (0.16 mole) of o-chlorophenol and 3 drops concentrated hydrochloric acid was heated on a steam both overnight. The oil was dissolved in methylene chloride and washed with three 50-ml. portions of 5% sodium hydroxide and one 50-ml. portion of water. The methylene chloride solution was dried over anhydrous sodium sulfate, concentrated and chromatographed on silica gel to give 8.9 g. (25%) of an oil as residue. The oil was converted to the hydrochloride and recrystallized from ethyl acetate-acetonitrile to yield white powder, m.p. 108°-110° C.

Workup

  1. additionA mixture of 17.0 g
  2. washwashed with three 50-ml
  3. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customchromatographed on silica gel
  6. customto give 8.9 g
  7. customrecrystallized from ethyl acetate-acetonitrile
  8. customto yield white powder, m.p. 108°-110° C.

Sources & evidence

ORD record
ord-ec7c2d8c19af46118928ad42a2593118
Source dataset
uspto-grants-1984_06
Patent number
US04452809

Reaction notes

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