Methyl iodide → 1,4-Dibenzyl-2-(methoxymethyl)piperazine

HRID 16874Notes

Reaction equation

HRID 16874 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH:11]1[CH2:23][OH:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:25]I>CN(C=O)C.CCOCC>[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH:11]1[CH2:23][O:24][CH3:25])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10827800(1,4-Dibenzylpiperazin-2-yl)methanol

Product 1

HCID 197635561,4-Dibenzyl-2-(methoxymethyl)piperazineYield 107%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.857 g, 21.42 mmol) was added portionwise to stirred Et2O (23.0 ml) at 25° C. under nitrogen. A solution of (1,4-dibenzylpiperazin-2-yl)methanol (1.411 g, 4.76 mmol) in DMF (8.0 ml) was added portionwise under nitrogen. The resulting suspension was stirred at room temperature for 1 h. A solution of methyl iodide (0.454 ml, 7.28 mmol) in Et2O (7.0 ml) was added dropwise to the reaction mixture at 10° C., under nitrogen. The resulting mixture was stirred at room temperature for 21 h. The reaction mixture was quenched with water (35 mL and extracted with Et2O (3×50 mL). The organic layers were combined and washed with water (50 mL), dried over MgSO4, filtered and evaporated to afford 1,4-dibenzyl-2-(methoxymethyl)piperazine (1.580 g, 107%) as a yellow oil. This was used directly without further purification.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 21 h
  2. customThe reaction mixture was quenched with water (35 mL
  3. extractionextracted with Et2O (3×50 mL)
  4. washwashed with water (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-f1feb73d474b408a946ed04454d26826
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

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