Methyl iodide → 1-Benzyl-3-benzylmethylaminomethyl-3-methoxypyrrolidine

HRID 2400084Notes

Reaction equation

HRID 2400084 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:14][NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[CH3:28]I>O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:14][NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([O:13][CH3:28])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19382195HCID 19382195, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 193821871-Benzyl-3-benzylmethylaminomethyl-3-methoxypyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

26 g (83 mmol) of crude 1-benzyl-3-benzylmethylaminomethyl-3-hydroxypyrrolidine in 50 ml of absolute tetrahydrofuran are added dropwise to 4 g of 80% strength sodium hydride in 100 ml of absolute tetrahydrofuran and the mixture is heated under reflux during this. After completion of hydrogen evolution, 12.4 g (87 mmol) of methyl iodide are slowly added dropwise and the mixture is subsequently heated overnight under reflux. The product is poured into ice water and extracted using toluene, the extract is dried over K2CO3 and concentrated, and the residue is distilled.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux during this
  3. temperatureunder reflux
  4. extractionextracted
  5. dry with materialthe extract is dried over K2CO3
  6. concentrationconcentrated
  7. distillationthe residue is distilled

Sources & evidence

ORD record
ord-f1d0454698244e9faedc91ef885d943a
Source dataset
uspto-grants-1995_09
Patent number
US05453422

Reaction notes

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