Dimethylamine → (1,4-Dibenzylpiperazin-2-yl)-N,N-dimethylmethanamine

HRID 1830030Notes

Reaction equation

HRID 1830030 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH2:21]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][NH:24][CH3:25]>C(O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH2:21][N:24]([CH3:25])[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 106631191,4-Dibenzyl-2-(chloromethyl)piperazine

Product 1

HCID 14664170(1,4-Dibenzylpiperazin-2-yl)-N,N-dimethylmethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1,4-bisbenzyl-2-(chloromethyl)piperazine (1 equivalent) and dimethylamine (5 equivalents) in ethanol, was heated at 150° C. for 36 hours in a sealed high pressure vessel. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was taken up in 1 N HCl, and the solution was washed with CH2Cl2. The water phase was made basic with a 30% aqueous NaOH solution (pH=12) and extracted with CH2Cl2. The organic extracts were collected and dried over Na2SO4. Evaporation of the solvent under reduced pressure afforded {[1,4-bisbenzylpiperazin-2-yl]methyl}dimethylamine. LC/MS (m/z): 324.3 (MH+), Rt 1.76 minutes.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. washthe solution was washed with CH2Cl2
  4. extractionextracted with CH2Cl2
  5. customThe organic extracts were collected
  6. dry with materialdried over Na2SO4
  7. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-a868db1b77ab444cabee03a302804e8d
Source dataset
uspto-grants-2006_06
Patent number
US07064215B2

Reaction notes

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