1,3-Propanediamine, N,N'-diphenyl- → HCID 12069779, compound

HRID 1368925Notes

Reaction equation

HRID 1368925 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]/[CH:15]=[CH:16]/[C:17](Cl)=[O:18])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[C:20]1([NH:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:37](=[O:40])([O-])O.[Na+]>C(Cl)Cl.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]/[CH:15]=[CH:16]/[C:17]([N:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:29][CH2:28][CH2:27][N:26]([C:37](=[O:40])/[CH:16]=[CH:15]/[CH:14]=[CH:13]/[C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:18])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 669161,3-Propanediamine, N,N'-diphenyl-HCID 516892Sodium BicarbonateHCID 22609552HCID 22609552, compound

Product 1

HCID 12069779HCID 12069779, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(3,4,5-trimethoxyphenyl)penta-(2E, 4E)-dienoyl chloride in methylene chloride (3 ml) was added dropwise to a solution of 68 mg (0.30 mmol) of N,N′-diphenyl-1,3-diaminopropane in pyridine (3 ml) with stirring in an ice bath. After completion of the addition, the mixture was stirred for an additional 1 hour, and a 5% aqueous solution (5 ml) of sodium hydrogencarbonate was added to the reaction mixture to conduct extraction with chloroform. An organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil (278 mg) was purified by column chromatography on silica gel, thereby obtaining 126 mg (yield: 59%) of the title compound as a colorless amorphous powder.

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred for an additional 1 hour
  3. extractionextraction with chloroform
  4. dry with materialAn organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant crude oil (278 mg) was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-19f8236f162342939b3608053cedfcda
Source dataset
uspto-grants-2003_06
Patent number
US06576642B2

Reaction notes

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