4-Chloroaniline → 1-(4-Chlorophenyl)ethane-1,2-diamine

HRID 1855991Notes

Reaction equation

HRID 1855991 reaction equation
OC(COC1C=CC=CC=1OC)CN1CCC([N:10]2[CH2:14][CH2:13][N:12](C3C=CC(Cl)=CC=3)C2=O)CC1.[Cl:33][C:34]1[CH:40]=[CH:39][C:37](N)=[CH:36][CH:35]=1.Br.BrCCN>C(C(CC)=O)C>[Cl:33][C:34]1[CH:40]=[CH:39][C:37]([CH:13]([NH2:12])[CH2:14][NH2:10])=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 27742172-Bromoethylamine hydrobromideHCID 23347353HCID 23347353, compound

Product 1

HCID 233473421-(4-Chlorophenyl)ethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 7288Ethyl ketoneSolvent

Conditions

Temperature
70 °C

Procedure

The 1-[2-hydroxy-3-(2-methoxyphenyloxy)-propyl]-4-[2-(4-chloroanilino)-ethylamino]-piperidine can be prepared as follows: A mixture of 38 g of p-chloroaniline and 31 g of 2-bromoethylamine-hydrobromide is heated to 70° C. with stirring. After 30 minutes 75 ml of diethyl ketone are added and the mixture is refluxed for 4 hours. The black solution is then concentrated under reduced pressure. The residue is made alkaline with 2 N sodium carbonate solution and extracted with three 100 ml portions of chloroform. The residual oil is fractionally distilled in vacuo to yield 1-(4-chlorophenyl)-ethylenediamine with a boiling point of 130°-135° C. (1.5 torr).

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. concentrationThe black solution is then concentrated under reduced pressure
  3. extractionextracted with three 100 ml portions of chloroform
  4. distillationThe residual oil is fractionally distilled in vacuo

Sources & evidence

ORD record
ord-0a6dd3ebc6f145e2bf583a446512c9c6
Source dataset
uspto-grants-1980_08
Patent number
US04217350

Reaction notes

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