Nitrogen mustard hydrochloride → 1-(2-Benzobicyclo[2.2.1]heptenyl)-4-methylpiperazine

HRID 1534432Notes

Reaction equation

HRID 1534432 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[CH2:8][C:7]=1[C:6]1[CH:9]=[CH:10][CH:11]=[CH:12][C:5]2=1.[CH3:13][N:14]([CH2:18][CH2:19]Cl)[CH2:15][CH2:16]Cl.Cl.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[C:7]12[CH2:8][C:4](=[CH:3][C:2]=1[N:1]1[CH2:19][CH2:18][N:14]([CH3:13])[CH2:15][CH2:16]1)[C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]2=1

Participants

6

Reactant 4

HCID 5935Nitrogen mustard hydrochlorideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 214136102-Aminobenzobicyclo[2.2.1]heptene

Product 1

HCID 1317171721-(2-Benzobicyclo[2.2.1]heptenyl)-4-methylpiperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Aminobenzobicyclo[2.2.1]heptene (1.1 g) was combined with mechlorethamine hydrochloride (1.4 g), potassium carbonate (1.5 g), and acetonitrile (25 ml) and heated to reflux for 24 hours. Water (50 ml) was added to the mixture and the resulting mixture was extracted with ether (3×50 ml). The combined ether solutions were dried over magnesium sulfate and the ether was removed on a rotary evaporator. The residue was combined with concentrated hydrochloric acid (5 ml) and 2-propanol (25 ml) and the solvent was removed on a rotary evaporator. The residue was suspended in 2-propanol and the solvent was removed on a rotary evaporator. This latter step was repeated. The residue was recrystallized from 2-propanol to provide the product as a tan solid. Analytical data are reported in Table I.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. extractionthe resulting mixture was extracted with ether (3×50 ml)
  4. dry with materialThe combined ether solutions were dried over magnesium sulfate
  5. customthe ether was removed on a rotary evaporator
  6. customthe solvent was removed on a rotary evaporator
  7. customthe solvent was removed on a rotary evaporator
  8. customThe residue was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-1a8fb60d68d04d768ecd8fdf291d9837
Source dataset
uspto-grants-1992_02
Patent number
US05089506

Reaction notes

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