Benzoyl chloride, 3,4-dichloro- → 3,4-Dichloro-N-[[1-(4-methyl-1-piperazinyl)cyclohexyl]methyl]-benzamide

HRID 2071996Notes

Reaction equation

HRID 2071996 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].[NH2:12][CH2:13][C:14]1([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH:12][CH2:13][C:14]1([N:20]2[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:6]

Participants

5

Reactant 2

HCID 76403Benzoyl chloride, 3,4-dichloro-HCID 70181321-[1-(4-METHYLPIPERAZIN-1-YL)CYCLOHEXYL]METHANAMINE

Product 1

HCID 542690043,4-Dichloro-N-[[1-(4-methyl-1-piperazinyl)cyclohexyl]methyl]-benzamideYield 49.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

A solution of 3,4-Dichlorobenzoylchloride (1.05 g.,) in benzene (10 ml) was added dropwise over 40 mins. to a stirred solution of 1-[1-(Aminomethyl)cyclohexyl]-4-methyl piperazine (1.06 g.,) in benzene (15 ml). The mixture was heated under reflux for 1 hr. on a steambath and the solution was evaporated. The solid residue was dissolved in ethanol, acidified with ethereal HCl and evaporated to give a white solid. This solid was suspended in water made alkaline with 5NNaOH and extracted with chloroform (x2). The combined chloroform extracts were dried (anhyd.Na 2 SO4) and evaporated. The solid residue was dissolved in hot petroleum ether (80°-100°) decolourised with charcoal and crystallised from petroleum ether (80°-100° ) to give 1-[1-(3,4 Dichlorobenzamido methyl) cyclohexyl] -4-methyl piperazine (0.95 g; 49%) m.p. 143° -146°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. customon a steambath and the solution was evaporated
  4. dissolutionThe solid residue was dissolved in ethanol
  5. customevaporated
  6. customto give a white solid
  7. extractionextracted with chloroform (x2)
  8. dry with materialThe combined chloroform extracts were dried (anhyd.Na 2 SO4)
  9. customevaporated
  10. dissolutionThe solid residue was dissolved in hot petroleum ether (80°-100°)
  11. customcrystallised from petroleum ether (80°-100° )

Sources & evidence

ORD record
ord-024bda8ce0e7428ba5c1411f0837bbc0
Source dataset
uspto-grants-1977_09
Patent number
US04049663

Reaction notes

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