Formic Acid → n-(4-((4-Phenylpiperazin-1-yl)methyl)phenylmethyl)formamide

HRID 1282052Notes

Reaction equation

HRID 1282052 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.C(OC=O)=O.[NH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)=[CH:20][CH:19]=1>C(Cl)Cl.C(OCC)(=O)C.C(O)C.C(O)(=O)C>[C:31]1([N:28]2[CH2:27][CH2:26][N:25]([CH2:24][C:21]3[CH:20]=[CH:19][C:18]([CH2:17][NH:16][CH:5]=[O:7])=[CH:23][CH:22]=3)[CH2:30][CH2:29]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

9

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 9548680Formic anhydrideHCID 184230964-((4-(Aminomethyl)phenyl)methyl)-1-phenylpiperazine

Product 1

HCID 18423173n-(4-((4-Phenylpiperazin-1-yl)methyl)phenylmethyl)formamide

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of acetic anhydride (0.36 ml) and formic acid (0.15 ml) was stirred at 50-60° C. for 2 hr, and to the obtained acetic acid and formic acid anhydride was added a solution of 4-((4-(aminomethyl)phenyl)methyl)-1-phenylpiperazine (0.5 g) in methylene chloride (10 ml) under ice-cooling. This reaction mixture was stirred at 5-10° C. for 2.5 hr and left standing at room temperature for 14 hr. To this reaction mixture were added ethanol (20 ml) and ethyl acetate (150 ml) and the mixture was washed with saturated sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a brown solid (0.56 g). The obtained solid was purified by silica gel column chromatography (developing solvent; chloroform:methanol=9:1) to give a pale-brown solid (0.55 g). The obtained solid was crystallized from ethyl acetate-hexane (2:1) to give the title compound (0.41 g) as pale-yellow white crystals, m.p.=108-109° C.

Workup

  1. temperaturecooling
  2. stirringThis reaction mixture was stirred at 5-10° C. for 2.5 hr
  3. waitleft
  4. waitstanding at room temperature for 14 hr
  5. washthe mixture was washed with saturated sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-448c95e95f414a7189b406e45453a965
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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