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Dicyclohexylcarbodiimide → HCID 21918641, compound

HRID 1250070
Notes
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Reaction equation

HRID 1250070 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:16]([C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:28]=1[OH:29])[C:23](O)=[O:24])([CH3:19])([CH3:18])[CH3:17].C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH3:33][C:30]([C:27]1[CH:26]=[C:22]([C:23]([N:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH2:12]2)=[O:24])[CH:21]=[C:20]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:28]=1[OH:29])([CH3:31])[CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 21918641HCID 21918641, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.07 g (10 mmoles) of 1-(4-nitrophenyl)piperazine, 2.5 g (10 mmoles) of 3,5-di-tert-butyl-4-hydroxybenzoic acid and 2.26 g (11 mmoles) of dicyclohexylcarbodiimide are introduced into a 100 ml flask containing 25 ml of DMF. The reaction medium is agitated for 15 hours at ambient temperature, the precipitate which appears is filtered out and rinsed with ethyl acetate. After concentration of the filtrate under reduced pressure, the residue is diluted in 20 ml of ethyl acetate and a new insoluble is eliminated by filtration. The solvent is evaporated off under vacuum and the residue is precipitated from diethyl ether. The solid is filtered, rinsed with 2×20 ml of ethyl acetate in order to obtain a yellow powder with a yield of 89%. Melting point: 159.5-160.5° C.

Workup

  1. filtrationthe precipitate which appears is filtered out
  2. washrinsed with ethyl acetate
  3. additionAfter concentration of the filtrate under reduced pressure, the residue is diluted in 20 ml of ethyl acetate
  4. filtrationa new insoluble is eliminated by filtration
  5. customThe solvent is evaporated off under vacuum
  6. customthe residue is precipitated from diethyl ether
  7. filtrationThe solid is filtered
  8. washrinsed with 2×20 ml of ethyl acetate in order
  9. customto obtain a yellow powder with a yield of 89%

Sources & evidence

ORD record
ord-301c6b42dbf042a6b60c278ad6258859
Source dataset
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06335445B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes