1-Methylpiperazine → HCID 19838942, compound

HRID 1639383Notes

Reaction equation

HRID 1639383 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]([C:10]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:11]=1[CH2:12][CH2:13][C:14]([OH:16])=O)=[O:9])(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>O1CCCC1>[Cl:21][C:18]1[CH:19]=[CH:20][C:10]([C:8]([CH2:7][CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])=[O:9])=[C:11]([CH2:12][CH2:13][C:14]([N:38]2[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]2)=[O:16])[CH:17]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 682631,1'-CarbonyldiimidazoleHCID 198331272-(4-Acetamidobutyryl)-5-chlorohydrocinnamic acid

Product 1

HCID 19838942HCID 19838942, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.10 g (0.01 mol) of 2-(4-acetamidobutyryl)-5-chlorohydrocinnamic acid and 1.70 g (0.011 mol) of 1,1'-carbonyldiimidazole are stirred at room temperature for 1 hour in 30 ml of tetrahydrofuran. Then, 1.2 ml (0.011 mol) of 1-methylpiperazine are added thereto at -70° and the mixture is left to warm to room temperature overnight. After concentration of the solution, the residue is extracted first with methylene chloride/2N hydrochloric acid and then with methylene chloride/concentrated aqueous ammonia solution, dried with sodium sulfate and the solvent is distilled in a vacuum. Chromatography on silica gel with methylene chloride-methanol (20:1) and crystallization from ethyl acetate/hexane gives N-[3-[4-chloro-2-[2-[(4methyl-piperazin-1-yl)carbonyl]ethyl]-benzoyl]propyl]acetamide as white crystals with melting point 126°-128°.

Workup

  1. waitat -70° and the mixture is left
  2. extractionAfter concentration of the solution, the residue is extracted first with methylene chloride/2N hydrochloric acid
  3. dry with materialwith methylene chloride/concentrated aqueous ammonia solution, dried with sodium sulfate
  4. distillationthe solvent is distilled in a vacuum
  5. customChromatography on silica gel with methylene chloride-methanol (20:1) and crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2106dc5d30944a48a6671765eb5d0ee0
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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