Hydrochloric Acid → HCID 18933590, compound

HRID 1598303Notes

Reaction equation

HRID 1598303 reaction equation
B.C1COCC1.[CH2:7]([N:14]([CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:21]=1[C:22]#[N:23])[CH3:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[ClH:29]>C1COCC1.CCOCC>[ClH:28].[ClH:29].[CH2:7]([N:14]([CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:21]=1[CH2:22][NH2:23])[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 18933642HCID 18933642, compound

Product 1

HCID 18933590HCID 18933590, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Borane/THF (165 ml of a 1M solution) was added with stirring to a solution of 2-[3-(N-benzyl-N-methylamino)propoxy]-6-chlorobenzonitrile (13.01 g) in dry THF (100 ml) under nitrogen at ambient temperature. The mixture was boiled under reflux for 5 hours and then evaporated to dryness. The residue was heated on a steam bath under nitrogen for 2 hours, then cooled to ambient temperature. 1M Hydrochloric acid (100 ml) was added and the mixture was heated on a steam bath for 2 hours. The mixture was cooled in ice and basified with concentrated sodium hydroxide solution and then 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 and recrystallised from propan-2-ol/IMS (2:1) to give 2-[3-(N-benzyl-N-methylamino)propoxy]-6-chlorobenzylamine dihydrochloride, m.p. 226°-228° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. customevaporated to dryness
  3. temperatureThe residue was heated on a steam bath under nitrogen for 2 hours
  4. addition1M Hydrochloric acid (100 ml) was added
  5. temperaturethe mixture was heated on a steam bath for 2 hours
  6. temperatureThe mixture was cooled in ice and basified with concentrated sodium hydroxide solution
  7. extractionextracted with dichloromethane
  8. customto give an oil
  9. customto give a solid which
  10. filtrationwas collected by filtration
  11. customrecrystallised from propan-2-ol/IMS (2:1)

Sources & evidence

ORD record
ord-6406e4a19a654f5abe9fcefe4550e3b5
Source dataset
uspto-grants-1998_04
Patent number
US05736568

Reaction notes

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