Hydrogen Bromide → HCID 18933633, compound

HRID 1598306Notes

Reaction equation

HRID 1598306 reaction equation
[CH2:1]([N:8]([CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][C:14]=1[CH2:15][N:16]([CH3:18])[CH3:17])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.[PH2](O)=O.[ClH:29]>CCOCC>[ClH:29].[ClH:29].[CH2:1]([N:8]([CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:14]=1[CH2:15][N:16]([CH3:18])[CH3:17])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 4124402Phosphinic AcidHCID 18933605HCID 18933605, compound

Product 1

HCID 18933633HCID 18933633, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-[2-(N-benzyl-N-methylamino)ethoxy]-5-methoxy-N,N-dimethylbenzylamine (1.0 g), aqueous hydrobromic acid (10 ml, 48%) and hypophosphorous acid (0.05 ml, 50% by weight aqueous solution) was boiled under reflux under nitrogen for 1 hour. The mixture was evaporated to dryness under reduced pressure and the residue was neutralised with saturated sodium bicarbonate solution and then basified to pH 9 with 2M sodium hydroxide solution. The mixture was extracted with dichloromethane to give a gum. The gum was purified by flash column chromatography on silica using ethyl acetate/methanol/triethylamine (18:2:1) as the mobile phase to give an oil which was dissolved in ether and acidified with ethereal hydrogen chloride to give a solid which was collected by filtration and then recrystallised from propan-2-ol to give 4-[2-(N-benzyl-N-methylamino)ethoxy]-3-(dimethylaminomethyl)phenol dihydrochloride, m.p. 199°-200° C.

Workup

  1. temperatureunder reflux under nitrogen for 1 hour
  2. customThe mixture was evaporated to dryness under reduced pressure
  3. extractionThe mixture was extracted with dichloromethane
  4. customto give a gum
  5. customThe gum was purified by flash column chromatography on silica
  6. customto give an oil which
  7. customto give a solid which
  8. filtrationwas collected by filtration
  9. customrecrystallised from propan-2-ol

Sources & evidence

ORD record
ord-5323e6634f52480c8f6f34811cdb3447
Source dataset
uspto-grants-1998_04
Patent number
US05736568

Reaction notes

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