Sodium Carbonate → HCID 14627771, compound

HRID 260598Notes

Reaction equation

HRID 260598 reaction equation
Cl.[Cl:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:4][CH2:5][CH2:6][C:7]#[N:8])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 22401913HCID 22401913, compound

Product 1

HCID 14627771HCID 14627771, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Bis-(4-chlorobenzyl)amine hydrochloride [prepared by reducing N-(4-chlorobenzyl)-4-chlorobenzamide with lithium aluminium hydride in tetrahydrofuran] was basified using sodium Carbonate in methylene dichloride solvent to give after rotary evaporation 3.16 g of the free base as an oil. This was then mixed with 4-bromobutyronitrile (1.19 ml), diisopropylethylamine (2.1 ml) and 25 ml of dry dimethylformamide and the mixture stirred at 80° C. under nitrogen for 24 hours. On cooling water (100cm3) was added and then the mixture was extracted with 1×50 ml and 2×25 ml of methylene dichloride. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to give an oil. This was further purified by column chromatography (silica column eluted with toluene) to give 2.83 g of the title product as an oil. 2.8 g of the title compound was dissolved in 10 ml hot ethanol, acidified with 0.76 g (1 equiv,) of oxalic acid, diluted with ether and cooled to give, after filtration, the 1:1-ethanedioate salt (1.78 g) as colourless crystals, mp 124°-6° (dec).

Workup

  1. customto give
  2. customafter rotary evaporation 3.16 g of the free base as an oil
  3. additionThis was then mixed with 4-bromobutyronitrile (1.19 ml), diisopropylethylamine (2.1 ml) and 25 ml of dry dimethylformamide
  4. temperatureOn cooling water (100cm3)
  5. additionwas added
  6. extractionthe mixture was extracted with 1×50 ml and 2×25 ml of methylene dichloride
  7. washThe combined extracts were washed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto give an oil
  12. customThis was further purified by column chromatography (silica column eluted with toluene)

Sources & evidence

ORD record
ord-d710ebb73277402da62ea55576ca2ed6
Source dataset
uspto-grants-1996_06
Patent number
US05527955

Reaction notes

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