Triethylamine → 1-Benzyl-4-phenyl-piperazine-2-carboxamide

HRID 728909Notes

Reaction equation

HRID 728909 reaction equation
[C:1]1([NH:7][CH2:8][CH2:9][NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:19]([CH2:23]Br)[C:20]([NH2:22])=[O:21].C(N(CC)CC)C.[OH-].[Na+]>C(OCC)C.CN(C)C=O>[C:1]1([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:19]([C:20]([NH2:22])=[O:21])[CH2:23]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 857982,3-DibromopropionamideHCID 5302982N-benzyl-N'-phenylethane-1,2-diamine

Product 1

HCID 109900971-Benzyl-4-phenyl-piperazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To dimethylformamide (300 mL) add N-phenyl-N'-phenylmethyl-1,2-ethanediamine (83 g, 0.37 mol), 2,3-dibromopropanamide (90 g, 0.39 mol) and triethylamine (41 g, 0.40 mol). Heat the resulting mixture at 110° C. and follow the progressof the reaction by thin-layer chromatography. Upon completion of the reaction add 1N NaOH until basic and add ethyl ether. Filter the precipitate that forms and recrystallize from 2-propanol to obtain the title compound.

Workup

  1. customthe reaction by thin-layer chromatography
  2. filtrationFilter the precipitate that forms
  3. customrecrystallize from 2-propanol

Sources & evidence

ORD record
ord-2563d0894aa240b59a86ea0471d3b78a
Source dataset
uspto-grants-1991_09
Patent number
US05051422

Reaction notes

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