2-Chloro-N,N-dimethylethylamine → Ethanamine, 2-((1,3-dihydro-6-methyl-4-(phenylmethyl)furo(3,4-c)pyridin-7-yl)oxy)-N,N-dimethyl-, dihydrochloride

HRID 1863260Notes

Reaction equation

HRID 1863260 reaction equation
[CH2:1]([C:8]1[C:13]2[CH2:14][O:15][CH2:16][C:12]=2[C:11]([OH:17])=[C:10]([CH3:18])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[H-].[Na+].[H][H].[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27][Cl:28]>CS(C)=O>[ClH:28].[ClH:28].[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27][O:17][C:11]1[C:12]2[CH2:16][O:15][CH2:14][C:13]=2[C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9][C:10]=1[CH3:18]

Participants

7

Reactant 5

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 5360545SodiumHCID 129409064-Benzyl-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-olHCID 178418361HCID 178418361, compound

Product 1

HCID 3052096Ethanamine, 2-((1,3-dihydro-6-methyl-4-(phenylmethyl)furo(3,4-c)pyridin-7-yl)oxy)-N,N-dimethyl-, dihydrochloride

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

12.1 g (50 millimoles) of 4-benzyl-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol are suspended in 40 ml of dry dimethylsulfoxide and converted to the sodium salt by adding 1.75 g (60 millimoles) of sodium hydride (85% strength) in oil at 20° C. When the evolution of hydrogen has ceased, 8.1 g (75 millimoles) of freshly distilled β-dimethylaminoethyl chloride are added dropwise and the mixture is left to stand for 15 hours at 10° C. The dimethylsulfoxide is distilled off in a high vacuum. The residue is taken up in methylene chloride, the salts and unconverted pyridinol are washed out with dilute sodium hydroxide solution and the methylene chloride phase is dried and concentrated under reduced pressure. The residue is converted to the hydrochloride by means of dilute hydrochloric acid and the hydrochloride is recrystallized from a mixture of ethanol and ether. 10.0 g of 4-benzyl-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-yl β-dimethylaminoethyl ether bis-hydrochloride, melting point 213° -214° C., are obtained.

Workup

  1. waitthe mixture is left
  2. distillationThe dimethylsulfoxide is distilled off in a high vacuum
  3. washthe salts and unconverted pyridinol are washed out with dilute sodium hydroxide solution
  4. dry with materialthe methylene chloride phase is dried
  5. concentrationconcentrated under reduced pressure
  6. customthe hydrochloride is recrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-43bc8b5e97124c339ad19442e75ba5ba
Source dataset
uspto-grants-1979_09
Patent number
US04168379

Reaction notes

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