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

HRID 887543Notes

Reaction equation

HRID 887543 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. The reaction mixture was cooled, the solid filtered and solvent evaporated. The residue was 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. temperatureThe reaction mixture was cooled
  2. filtrationthe solid filtered
  3. customsolvent evaporated
  4. additionThe residue was diluted 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-f2410400e1cb46b7a3a3958f1318a580
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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