Mechlorethamine → 1-(2-(tert-Butyl)phenyl)-4-methylpiperazine

HRID 238468Notes

Reaction equation

HRID 238468 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:13][CH2:14][N:15]([CH2:17][CH2:18]Cl)[CH3:16].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>COCCOCCOC>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:18][CH2:17][N:15]([CH3:16])[CH2:14][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 4033MechlorethamineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 805742-tert-Butylaniline

Product 1

HCID 219596701-(2-(tert-Butyl)phenyl)-4-methylpiperazine

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
170 °C

Procedure

2-tert-Butyl-phenylamine and bis-(2-chloro-ethyl)-methylamine were mixed together with K2CO3 (25 g), NaI (10 g) and diglyme (250 mL) and heated at 170° C. for 8 h. Cooled and filtered solid and evaporated solvent. Diluted with EtOAc, washed with NaHCO3 solution, extracted twice more with EtOAc, washed with brine, dried over Na2SO4 and evaporated to give the compound as a dark solid.

Workup

  1. temperatureCooled
  2. filtrationfiltered solid
  3. customevaporated solvent
  4. additionDiluted with EtOAc
  5. washwashed with NaHCO3 solution
  6. extractionextracted twice more with EtOAc
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-8ebcf48ce69e4804913fe8ac86c3e58c
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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