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 1706014Notes

Reaction equation

HRID 1706014 reaction equation
[CH2:1]([C:8]1[C:13]2[CH2:14][CH2:15][O: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:14]2[CH2:15][O:16][CH2:12][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 20336508HCID 20336508, compoundHCID 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-dihydro-furo[3,2-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 organic 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 ethanol/ether. 10.0 g of 4-benzyl-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-yl β-dimethylaminoethyl ether bis-hydrochloride are obtained; melting point 213°-214° C.

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. customthe organic phase is dried
  5. concentrationconcentrated under reduced pressure
  6. customthe hydrochloride is recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-2514914f14e347b09f498a5b3f12d8a4
Source dataset
uspto-grants-1980_06
Patent number
US04206117

Reaction notes

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