Hydrochloric Acid → HCID 18933625, compound

HRID 1598308Notes

Reaction equation

HRID 1598308 reaction equation
B.C1COCC1.[CH2:7]([N:14]([CH2:16][CH2:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:20]=1[C:21]#[N:22])[CH3:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C1COCC1.CCOCC>[CH2:7]([N:14]([CH2:16][CH2:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:20]=1[CH2:21][NH2:22])[CH3:15])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 18933638HCID 18933638, compound

Product 1

HCID 18933625HCID 18933625, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane/THF (80 ml, 1M solution) was added to a solution of 2-[2-(N-benzyl-N-methylamino) ethoxy]-6-chlorobenzonitrile (6.02 g) in THF (60 ml) at ambient temperature under nitrogen with stirring. The mixture was stirred at ambient temperature for 4 hours and then boiled under reflux for 1 hour. The mixture was evaporated to dryness and the residue was heated on a steam bath under nitrogen for 1 hour and then 1M hydrochloric acid (100 ml) was added and the mixture was heated for a further 2 hours. The mixture was cooled, washed with ethyl acetate, basified with concentrated sodium hydroxide solution and extracted with dichloromethane to give an oil. The oil was dissolved in ether and treated with ethereal hydrogen chloride to give a solid which was collected by filtration. The solid was stirred with 2M sodium hydroxide solution and then extracted with dichloromethane to give an oil which was distilled under vacuum. The oil which boiled at 140° C. at 0.04 mbar was dissolved in ether and treated with ethereal hydrogen chloride. The precipitated solid was collected by filtration and dried to give 2-[2-(N-benzyl-N-methylamino)ethoxy]-6-chlorobenzylamine, m.p. 85° C.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 4 hours
  2. temperatureunder reflux for 1 hour
  3. customThe mixture was evaporated to dryness
  4. temperaturethe residue was heated on a steam bath under nitrogen for 1 hour
  5. addition1M hydrochloric acid (100 ml) was added
  6. temperaturethe mixture was heated for a further 2 hours
  7. temperatureThe mixture was cooled
  8. washwashed with ethyl acetate
  9. extractionextracted with dichloromethane
  10. customto give an oil
  11. customto give a solid which
  12. filtrationwas collected by filtration
  13. stirringThe solid was stirred with 2M sodium hydroxide solution
  14. extractionextracted with dichloromethane
  15. customto give an oil which
  16. distillationwas distilled under vacuum
  17. dissolutionThe oil which boiled at 140° C. at 0.04 mbar was dissolved in ether
  18. additiontreated with ethereal hydrogen chloride
  19. filtrationThe precipitated solid was collected by filtration
  20. customdried

Sources & evidence

ORD record
ord-f19987a4ee7c46e0b35bde918ab89f97
Source dataset
uspto-grants-1998_04
Patent number
US05736568

Reaction notes

Loading…