Bis(2-chloroethyl)amine → HCID 20332012, compound

HRID 2057363Notes

Reaction equation

HRID 2057363 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6]Cl.[Cl:8][C:9]1[CH:10]=[C:11]([NH2:23])[CH:12]=[CH:13][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[ClH:1].[Cl:8][C:9]1[CH:10]=[C:11]([N:23]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH:12]=[CH:13][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 9533Bis(2-chloroethyl)amineHCID 11430Potassium CarbonateHCID 906443-Chloro-4-(4-chlorophenoxy)aniline

Product 1

HCID 20332012HCID 20332012, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 9 parts of 2-chloro-N-(2-chloroethyl)ethanamine hydrochlorine, 12.7 parts of 3-chloro-4-(4-chlorophenoxy)-benzenamine and 28 parts n-butanol is stirred and refluxed for 24 hours. The mixture is cooled and 3.5 parts of potassium carbonate are added. Stirring is continued for another 24 hours at reflux. The reaction mixture is filtered hot and the product is crystallized after cooling the filtrate. 2,2'-Oxybispropane is added and the precipitated product is filtered off. It is crystallized from a mixture of 2-propanol and 2,2'-oxybispropane, yielding 10.5 parts of 1-[3-chloro-4-(4-chlorophenoxy)phenyl]piperazine hydrochloride; mp. 187.7° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureThe mixture is cooled
  3. stirringStirring
  4. temperatureat reflux
  5. filtrationThe reaction mixture is filtered hot
  6. customthe product is crystallized
  7. temperatureafter cooling the filtrate
  8. addition2,2'-Oxybispropane is added
  9. filtrationthe precipitated product is filtered off
  10. customIt is crystallized from a mixture of 2-propanol and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-740f776a47494834b16e057b8b3c072e
Source dataset
uspto-grants-1980_07
Patent number
US04210646

Reaction notes

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