1-Methylpiperazine → HCID 58790234, compound

HRID 418616Notes

Reaction equation

HRID 418616 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]([CH3:11])[CH2:8][CH2:9]Cl)=[CH:4][CH:3]=1.[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>COCCOC.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]([CH3:11])[CH2:8][CH2:9][N:18]2[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 587903924-Bromo-N-(2-chloroethyl)-N-methylbenzenemethanamine

Product 1

HCID 58790234HCID 58790234, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 73 (3.5 g, 13.3 mmol) in DME (20 ml) was added N-methylpiperazine (3.33 g, 2.5 eq, 33.3 mmol) and tetrabutylammonium bromide (cat). The reaction mixture was heated to reflux for 3 hrs, then cooled to RT and concentrated. The crude was dissolved in EtOAc, washed well with water and the organic phase was collected, dried over Na2SO4 and filtered then concentrated. Purification by column chromatography (20% MeOH in EtOAc+1% TEA) afforded 74 as colorless oil (3.0 g, 69% yield). MS (m/z): 326.0/328.0 (M+H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hrs
  3. concentrationconcentrated
  4. dissolutionThe crude was dissolved in EtOAc
  5. washwashed well with water
  6. customthe organic phase was collected
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthen concentrated
  10. customPurification by column chromatography (20% MeOH in EtOAc+1% TEA)

Sources & evidence

ORD record
ord-cc47b3174e814604b746ecf7f09820ae
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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