Chlorambucil → HCID 11825264, compound

HRID 1743078Notes

Reaction equation

HRID 1743078 reaction equation
S(Cl)(Cl)=O.[CH:5]1[C:10]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[CH:9][CH:8]=[C:7]([N:17]([CH2:21][CH2:22][Cl:23])[CH2:18][CH2:19][Cl:20])[CH:6]=1.[CH3:24][N:25]([CH3:30])[CH2:26][CH2:27][CH2:28][NH2:29]>ClCCl>[CH3:24][N:25]([CH3:30])[CH2:26][CH2:27][CH2:28][NH:29][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][C:10]1[CH:5]=[CH:6][C:7]([N:17]([CH2:21][CH2:22][Cl:23])[CH2:18][CH2:19][Cl:20])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 2708ChlorambucilHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 24386Thionyl Chloride

Product 1

HCID 11825264HCID 11825264, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
4 °C

Procedure

1.25 ml of thionyl chloride is added at 0° C., under an inert atmosphere, to a solution of 1.61 mmol of chlorambucil in 5 ml of dichloromethane The reaction mixture is stirred at 4° C. for 16 hours and then excess SOCl2 is evaporated off under reduced pressure. The residue obtained is taken up in 10 ml of dichloromethane. 1.61 mmol of 3-(dimethyl-amino)propylamine dissolved in 10 ml of dichloromethane are added to the resulting solution at 0° C. under an inert atmosphere. The mixture is then stirred at ambient temperature for 1 hour. At the end of that time, a second addition of 1.61 mmol of diamine is carried out. After 4 hours' stirring, the reaction mixture is evaporated under reduced pressure. Following neutralisation with a 1N NaHCO3 solution, the aqueous phase is extracted several times with dichloromethane. The different organic phases are combined, washed with water until neutral, dried, filtered and evaporated under reduced pressure. The residue obtained is purified by chromatography on silica gel (eluant: gradient of ethanol in dichloromethane starting from 0 and going up to 50% and then, to finish, the eluant: dichloromethane/ethanol/ammonia, 50/49/1, is used). The expected product is obtained in the form of an oil.

Workup

  1. customexcess SOCl2 is evaporated off under reduced pressure
  2. customThe residue obtained
  3. additionare added to the resulting solution at 0° C. under an inert atmosphere
  4. stirringThe mixture is then stirred at ambient temperature for 1 hour
  5. stirringAfter 4 hours' stirring
  6. customthe reaction mixture is evaporated under reduced pressure
  7. extractionthe aqueous phase is extracted several times with dichloromethane
  8. washwashed with water until neutral,
  9. customdried
  10. filtrationfiltered
  11. customevaporated under reduced pressure
  12. customThe residue obtained
  13. customis purified by chromatography on silica gel (eluant

Sources & evidence

ORD record
ord-f1302f4a9891416ba286d0d3770962a4
Source dataset
uspto-grants-2006_03
Patent number
US07008613B2

Reaction notes

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