1-Chloro-4-(chloromethyl)benzene → HCID 20379913, compound

HRID 1448479Notes

Reaction equation

HRID 1448479 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[C:10]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)#[C:11][CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:16]2[CH2:17][CH2:18][N:13]([C:10]#[C:11][CH3:12])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 10340Sodium CarbonateHCID 20379915HCID 20379915, compound

Product 1

HCID 20379913HCID 20379913, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.44 g. of 4-chlorobenzyl chloride, 4.97 g. of N-propynyl piperazine, 8.48 g. of sodium carbonate and 50 ml. of ethanol was refluxed for 18 hours. The mixture was then filtered and the filtrate evaporated in vacuo. The residual oil was dissolved in chloroform which solution was washed with water and then dried over magnesium sulfate. The mixture was then filtered and the filtrate was evaporated under vacuum and subsequently distilled to give a yellow oil of the expected N'-(4-chlorobenzyl)-N-propynyl piperazine, b.p. 162°-5° C./1.5 mm, which produces a single spot of T.L.C. and the expected NMR and IR spectra.

Workup

  1. additionA mixture of 6.44 g
  2. filtrationThe mixture was then filtered
  3. customthe filtrate evaporated in vacuo
  4. dissolutionThe residual oil was dissolved in chloroform which solution
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe mixture was then filtered
  8. customthe filtrate was evaporated under vacuum
  9. distillationsubsequently distilled

Sources & evidence

ORD record
ord-d80a6bc128ba4b2c9e9af76bf3d2681d
Source dataset
uspto-grants-1979_12
Patent number
US04180574

Reaction notes

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