N,N-Diethyl-p-phenylenediamine → N-(4-Diethylamino-phenyl)-2-phenyl-2-pyridin-4-yl-acetamide

HRID 2186765Notes

Reaction equation

HRID 2186765 reaction equation
C[Al](C)C.[CH2:5]([N:7]([CH2:15][CH3:16])[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)[CH3:6].C([O:19][C:20](=O)[CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)C>C1(C)C=CC=CC=1.ClCCCl>[CH2:15]([N:7]([CH2:5][CH3:6])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:20](=[O:19])[CH:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:10][CH:9]=1)[CH3:16]

Participants

6

Reactant 3

HCID 7120N,N-Diethyl-p-phenylenediamineHCID 12870789Phenyl-pyridin-4-yl-acetic acid ethyl esterHCID 16682925Trimethylaluminum

Product 1

HCID 9820225N-(4-Diethylamino-phenyl)-2-phenyl-2-pyridin-4-yl-acetamideYield 32.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Trimethylaluminum (2.0 mL of a 2.0 M solution in toluene, 4.0 mmol, 3.0 equiv) was added to a solution of N,N-diethyl-1,4-phenylenediamine (0.68 mL, 4.0 mmol, 3.0 equiv) in 1,2-dichloroethane (10 mL). The resultant solution was stirred at 23° C. for 30 minutes, and then phenyl-pyridin-4-yl-acetic acid ethyl ester (330 mg, 1.36 mmol, 1.0 equiv) was added. The reaction mixture was heated to 60° C. for 19 hours, cooled to 23° C., and quenched with 1 N aqueous tartaric acid. The pH of the reaction mixture was adjusted to 5, and the reaction mixture was extracted with three portions of ethyl acetate (50 mL). The combined organic extracts were dried over magnesium sulfate and were concentrated. Purification of the residue by flash column chromatography (20% THF/hexanes grading to 100% THF) provided N-(4-Diethylamino-phenyl)-2-phenyl-2-pyridin-4-yl-acetamide (160 mg). MS: 360 (M+1)

Workup

  1. temperaturecooled to 23° C.
  2. customquenched with 1 N aqueous tartaric acid
  3. extractionthe reaction mixture was extracted with three portions of ethyl acetate (50 mL)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. concentrationwere concentrated
  6. customPurification of the residue by flash column chromatography (20% THF/hexanes grading to 100% THF)

Sources & evidence

ORD record
ord-7483f30243704a61b58cf13b72eafe86
Source dataset
uspto-grants-2002_06
Patent number
US06407120B1

Reaction notes

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