Sodium Chloride → HCID 10809774, compound

HRID 743344Notes

Reaction equation

HRID 743344 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[OH:22])[CH:11]=[CH:12][CH:13]=1.[Cl-].[Na+].Cl.Cl[CH2:27][CH2:28][CH:29]1[CH2:33][CH2:32][CH2:31][N:30]1[CH3:34]>CC(N(C)C)=O.O.C(OCC)(=O)C>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH2:27][CH2:28][CH:29]2[CH2:33][CH2:32][CH2:31][N:30]2[CH3:34])[CH:11]=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 10537566HCID 10537566, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10809774HCID 10809774, compoundYield 52.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

1.06 g of potassium t-butoxide were added to a solution of 1.00 g of 2-[2-(3-chlorophenyl)ethyl]phenol (prepared as described in Preparation 44) in 20 ml of dimethylacetamide, whilst cooling by ice and sodium chloride and stirring. 0.949 g of 2-(2-chloroethyl)-1-methylpyrrolidine hydrochoride was then added to the solution, and the mixture was stirred at 50° C. for 3 hours. At the end of this time, the reaction mixture was cooled, and 100 ml of ethyl acetate and 50 ml of water were added to the mixture, which was then shaken. The ethyl acetate layer was separated, washed twice with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The ethyl acetate layer was then concentrated by distillation under reduced pressure, and the concentrate was purified by column chromatography through silica gel, using a 20:1 by volume mixture of methylene chloride and methanol as the eluent, to give 0.770 g (yield 52%) of the title compound as a colorless oil.

Workup

  1. stirringthe mixture was stirred at 50° C. for 3 hours
  2. temperatureAt the end of this time, the reaction mixture was cooled
  3. stirringwas then shaken
  4. customThe ethyl acetate layer was separated
  5. washwashed twice with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe ethyl acetate layer was then concentrated by distillation under reduced pressure
  8. customthe concentrate was purified by column chromatography through silica gel
  9. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-ddb496c997054efe9da7173edfb7acd8
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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