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Dicyclohexylcarbodiimide → (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-[3-(1-pyrrolyl)benzoylamino]benzylamine

HRID 2254414
Notes
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Reaction equation

HRID 2254414 reaction equation
[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[CH:13]=1)[CH2:9][CH3:10].[N:21]1([C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29](O)=[O:30])[CH:25]=[CH:24][CH:23]=[CH:22]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.O1CCCC1>[CH3:20][C:2]([CH3:19])([CH3:1])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:29](=[O:30])[C:28]2[CH:32]=[CH:33][CH:34]=[C:26]([N:21]3[CH:25]=[CH:24][CH:23]=[CH:22]3)[CH:27]=2)[CH:13]=1)[CH2:9][CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 7365373-(1H-pyrrol-1-yl)benzoic acidHCID 19917001(E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-aminobenzylamine

Product 1

HCID 19744790(E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-[3-(1-pyrrolyl)benzoylamino]benzylamineYield 72.6%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

83 mg of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-aminobenzylamine and 100 mg of 3-(1-pyrrolyl)benzoic acid were dissolved in a mixture of 1 ml of methylene chloride and 2 ml of tetrahydrofuran, and 92 mg of N,N'-dicyclohexylcarbodiimide (DCC) was added. The mixture was stirred at room temperature for 3 hours. The reaction mixture was evaporated under reduced pressure, and the residue was dissolved in methylene chloride. The insoluble material was separated by filtration, and washed successively with a 5% aqueous solution of sodium hydrogen carbonate, 5% hydrochloric acid and a saturated aqueous solution of sodium chloride. It was dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography [Wakogel C-200, 20 g; eluting solvent: hexane/-ethyl acetate =10/1 → 3/1] to give 98 mg (yield 61%) of the captioned compound as a pale yellow oil.

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride
  4. customThe insoluble material was separated by filtration
  5. washwashed successively with a 5% aqueous solution of sodium hydrogen carbonate, 5% hydrochloric acid
  6. dry with materialIt was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified by silica gel column chromatography [Wakogel C-200, 20 g; eluting solvent: hexane/-ethyl acetate =10/1 → 3/1]

Sources & evidence

ORD record
ord-ec1a59457cb04297947edbdc7f11d249
Source dataset
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05234946

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes