Sodium Carbonate → HCID 14627771, compound

HRID 1109553Notes

Reaction equation

HRID 1109553 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+]>>[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

3

Reactant 2

HCID 10340Sodium CarbonateHCID 22401913HCID 22401913, compound

Product 1

HCID 14627771HCID 14627771, compound

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 dichlorlde 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 (100 cm3) 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 (100 cm3)
  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-d46c9941262c435f8f8f98523b5a65cd
Source dataset
uspto-grants-1994_06
Patent number
US05321047

Reaction notes

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