Methyl iodide → 2-(1-Methoxyethyl)-1,4-bis(phenylmethyl)piperazine

HRID 35315Notes

Reaction equation

HRID 35315 reaction equation
[CH3:1][CH:2]([CH:4]1[CH2:9][N:8]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6][N:5]1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[OH:3].[H-].[Na+].I[CH3:27]>CN(C)C=O>[CH3:27][O:3][CH:2]([CH:4]1[CH2:9][N:8]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6][N:5]1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21295699(1,4-Dibenzyl-piperazin-2-yl)-ethanol

Product 1

HCID 212957062-(1-Methoxyethyl)-1,4-bis(phenylmethyl)piperazineYield 71.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 60.5 parts of α-methyl-1,4-bis(phenylmethyl)-2-piperazinemethanol and 180 parts of N,N-dimethylformamide were added portionwise 29.8 parts of a sodium hydride dispersion 50% at a temperature below 35° C. under nitrogen atmosphere. The mixture was allowed to cool and stirred for 3 hours at room temperature. After cooling to 10° C., there were added dropwise 9.4 parts of iodomethane at about 20° C. Upon completion, stirring was continued for 2 hours at room temperature. The reaction mixture was poured onto water and the product was extracted twice with 1,1'-oxybisethane. The combined extracts were washed with water, dried, filtered and evaporated, yielding 45.2 parts (71.5%) of 2-(1-methoxyethyl)-1,4-bis(phenylmethyl)piperazine as a residue (intermediate 28).

Workup

  1. temperatureto cool
  2. temperatureAfter cooling to 10° C.
  3. stirringUpon completion, stirring
  4. waitwas continued for 2 hours at room temperature
  5. additionThe reaction mixture was poured onto water
  6. extractionthe product was extracted twice with 1,1'-oxybisethane
  7. washThe combined extracts were washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-de2efa54aeb44026a641832766aa2f0a
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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