Pyrrolidine → HCID 19007225, compound

HRID 1614555Notes

Reaction equation

HRID 1614555 reaction equation
[Cl:1][CH2:2][Si:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:5])[CH3:4].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>C1(C)C(C)=CC=CC=1>[ClH:1].[CH2:6]([Si:3]([CH2:2][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)([CH3:5])[CH3:4])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 4046821Benzyl(chloromethyl)dimethylsilane

Product 1

HCID 19007225HCID 19007225, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

9.9 g of chloromethyl-benzyl-dimethylsilane and 8.9 g of pyrrolidine are refluxed in 40 ml of xylene for 6 hours, then the reaction mixture is washed 5 times with a total of 250 ml of water at room temperature. The organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated to solvent-free. The slightly yellow oily residue is dissolved in 20 ml of ethyl acetate and the solution is acidified to pH 4.5 by adding ethanolic hydrogen chloride solution. After drying the precipitate the named product is obtained in a yield of 11.3 g (94%), m.p.: 140°-140.5° C.

Workup

  1. washthe reaction mixture is washed 5 times with a total of 250 ml of water at room temperature
  2. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe filtrate is evaporated to solvent-free
  5. dissolutionThe slightly yellow oily residue is dissolved in 20 ml of ethyl acetate
  6. additionby adding ethanolic hydrogen chloride solution
  7. customAfter drying the precipitate the named product
  8. customis obtained in a yield of 11.3 g (94%), m.p.: 140°-140.5° C.

Sources & evidence

ORD record
ord-aad0810be50f4cc2b32fcd1345a46597
Source dataset
uspto-grants-1993_03
Patent number
US05198446

Reaction notes

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