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 1156398Notes

Reaction equation

HRID 1156398 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 mmoles) of 4-benzyl-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-ol (compare Example 8, stage 1) are suspended in 40 ml of dry dimethylsulfoxide and converted to the sodium salt by adding 1.75 g (60 mmoles) of sodium hydride (85% strength in oil) at 20° C. When the evolution of hydrogen has ceased, 8.1 g (75 mmoles) 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 then distilled off under greatly reduced pressure. The residue is taken up in methylene chloride, the salts and the 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, by means of dilute hydrochloric acid, into the hydrochloride, which is recrystallized from an ethanol/ether mixture. 10.0 g of 4-benzyl-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-yl β-dimethylaminoethyl ether bis-hydrochloride, of melting point 213°-214° C., are obtained.

Workup

  1. waitthe mixture is left
  2. distillationThe dimethylsulfoxide is then distilled off under greatly reduced pressure
  3. washthe salts and the unconverted pyridinol are washed out with dilute sodium hydroxide solution
  4. customthe organic phase is dried
  5. concentrationconcentrated under reduced pressure
  6. customis recrystallized from an ethanol/ether mixture

Sources & evidence

ORD record
ord-e93878e4b4a9491bbb326f85a1f09264
Source dataset
uspto-grants-1982_06
Patent number
US04335241

Reaction notes

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