Chloroform → n-(4-((4-Phenylpiperazin-1-yl)methyl)phenylmethyl)propionamide

HRID 1282053Notes

Reaction equation

HRID 1282053 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:5][CH:4]=1.[C:22](Cl)(=[O:25])[CH2:23][CH3:24].C(N(CC)CC)C.C(Cl)(Cl)Cl>C(Cl)Cl>[C:16]1([N:13]2[CH2:12][CH2:11][N:10]([CH2:9][C:6]3[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:22](=[O:25])[CH2:23][CH3:24])=[CH:8][CH:7]=3)[CH2:15][CH2:14]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 184230964-((4-(Aminomethyl)phenyl)methyl)-1-phenylpiperazine

Product 1

HCID 18423175n-(4-((4-Phenylpiperazin-1-yl)methyl)phenylmethyl)propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-((4-(aminomethyl)phenyl)methyl)-1-phenylpiperazine (0.62 g), propionyl chloride (0.23 ml) and triethylamine (0.37 ml) in methylene chloride (20 ml) was stirred at room temperature for 4 hr. To this reaction mixture was added chloroform (100 ml), and the mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a pale-brown solid (0.9 g). The obtained solid was crystallized from ethyl acetate (50 ml) to give the title compound (0.5 g) as pale-yellow white crystals, m.p.=140-141° C.

Workup

  1. washthe mixture was washed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-abd1348a7181451da84653080cd7a198
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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