Hydrochloric Acid → HCID 14319497, compound

HRID 1439363Notes

Reaction equation

HRID 1439363 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1.Cl>C(Cl)(Cl)Cl>[CH3:22][N:19]1[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][CH2:13][NH:12][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69772,5-DichloronitrobenzeneHCID 783281-(3-Aminopropyl)-4-methylpiperazine

Product 1

HCID 14319497HCID 14319497, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2,5-dichloronitrobenzene (95.5 g., 0.497 mole) and 1-(3-aminopropyl)-4-methylpiperazine (82.2 g., 0.522 mole) was heated in a nitrogen atmosphere at 130° C. for 5 hours and cooled to room temperature. The mixture was poured into a separatory funnel containing 1500 ml. of 3N HCl and 500 ml. chloroform. After shaking and separation of layers, the chloroform was withdrawn and the aqueous layer extracted with fresh CHCl3. The aqueous layer was made alkaline with 20% NaOH and the resulting oil extracted with 3 × 600 ml. CHCl3. The combined extracts were dried over Na2SO4 and the solvent evaporated at reduced pressure to give 131.5 g. (85% yield) of 2-[3-(4-methyl-1-piperazinyl)propylamino]-5-chloronitrobenzene as a dark orange oil.

Workup

  1. temperaturecooled to room temperature
  2. additionThe mixture was poured into a separatory funnel
  3. additioncontaining 1500 ml
  4. customseparation of layers
  5. customthe chloroform was withdrawn
  6. extractionthe aqueous layer extracted with fresh CHCl3
  7. extractionthe resulting oil extracted with 3 × 600 ml
  8. dry with materialThe combined extracts were dried over Na2SO4
  9. customthe solvent evaporated at reduced pressure
  10. customto give 131.5 g

Sources & evidence

ORD record
ord-eb1085b3ac1e43f199f645c3b6f14319
Source dataset
uspto-grants-1977_11
Patent number
US04059584

Reaction notes

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