Water → 2-[2-Methoxy-2-(3-methoxyphenyl)-ethyl]-1-methylpyrrolidine

HRID 2049658Notes

Reaction equation

HRID 2049658 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([OH:17])[CH2:10][CH:11]2[CH2:15][CH2:14][CH2:13][N:12]2[CH3:16])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH3:20]I.O>CN(C)C=O>[CH3:20][O:17][CH:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:10][CH:11]1[CH2:15][CH2:14][CH2:13][N:12]1[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 30543491-(3-Methoxyphenyl)-2-(1-methylpyrrolidin-2-yl)ethan-1-ol

Product 1

HCID 203441532-[2-Methoxy-2-(3-methoxyphenyl)-ethyl]-1-methylpyrrolidineYield 66.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.0 g of 1-(3-methoxyphenyl)-2-(1-methyl-2-pyrrolidinyl)-ethanol dissolved in 15 ml of dimethyl formamide is added dropwise within 5 minutes, with stirring and exclusion of moisture, to a suspenion of 0.25 g of 80 p.c. sodium hydride. Stirring is effected for 30 minutes and a solution of 0.85 g methyl iodide in 10 ml of dimethyl formamide is added drop by drop. The mixture is kept at 60° for 2 hours, treated with water and extracted with diethyl ether. The etheral phase is concentrated. There are obtained 0.7 g of the title compound as oily mixture of diastereoisomers.

Workup

  1. additionis added dropwise within 5 minutes
  2. stirringStirring
  3. waitThe mixture is kept at 60° for 2 hours
  4. extractionextracted with diethyl ether
  5. concentrationThe etheral phase is concentrated

Sources & evidence

ORD record
ord-2f87fa20f31f49829818229d5537eb11
Source dataset
uspto-grants-1980_04
Patent number
US04198424

Reaction notes

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