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

HRID 1283540
Notes
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Reaction equation

HRID 1283540 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-methylpiperazin-1-yl)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.Na2SO4) 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.Na2SO4)
  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-7ce52a3ed0c24610ac21d4ddb4fae2a6
Source dataset
uspto-grants-1976_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03975443

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes