1,1-Dichloroethane → HCID 15622949, compound

HRID 2108155Notes

Reaction equation

HRID 2108155 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][O:4][CH2:5][CH:6]([OH:13])[CH2:7][N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.ClC(Cl)C.S(Cl)(Cl)=O.[OH-].[Na+]>>[CH3:14][CH:2]([CH3:1])[CH2:3][O:4][CH2:5][CH:6]([OH:13])[CH2:7][N:8]([CH2:9][CH3:10])[CH2:12][CH3:11]

Participants

5

Reactant 4

HCID 63651,1-Dichloroethane2×HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 64521401-(2-Methylpropoxy)-3-(pyrrolidin-1-yl)propan-2-ol

Product 1

HCID 15622949HCID 15622949, compound

Procedure

10 g. 3-(2-Methylpropoxy)-1-pyrrolidinopropan-2-ol are dissolved in 100 ml. dichloroethane. A solution of 7.1 g. thionyl chloride in 20 ml. dichloroethane is added dropwise thereto, while stirring, and the reaction mixture subsequently heated for 2 hours to 70° C. The reaction mixture is cooled, poured on to ice water and subsequently rendered alkaline by the addition of a concentrated aqueous solution of sodium hydroxide. The organic phase is separated off and the aqueous phase again extracted with methylene chloride. The organic phases are combined, dried over anhydrous sodium sulphate and evaporated. The residue is purified by chromatography on a silica gel column (elution agent: methylene chloride/5% methanol). There are obtained 9 g. of the title compound in the form of an oily product.

Workup

  1. temperaturethe reaction mixture subsequently heated for 2 hours to 70° C
  2. temperatureThe reaction mixture is cooled
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase again extracted with methylene chloride
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated
  7. customThe residue is purified by chromatography on a silica gel column (elution agent: methylene chloride/5% methanol)
  8. customThere are obtained 9 g

Sources & evidence

ORD record
ord-d615683bff344a25be33b34441f96338
Source dataset
uspto-grants-1990_06
Patent number
US04937337

Reaction notes

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