3,3-Diphenylpropylamine → Ethyl (3-{3-[(3,3-diphenylpropyl)amino]propyl}phenoxy)acetate

HRID 2389317Notes

Reaction equation

HRID 2389317 reaction equation
I[CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:15]=[CH:16][CH:17]=1)[O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[C:18]1([CH:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:25][CH2:26][NH2:27])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.CCOC(C)=O>[C:28]1([CH:24]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:25][CH2:26][NH:27][CH2:2][CH2:3][CH2:4][C:5]2[CH:6]=[C:7]([CH:15]=[CH:16][CH:17]=2)[O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 796983,3-DiphenylpropylamineHCID 86637892Ethyl [3-(3-iodopropyl)phenoxy]acetate

Product 1

HCID 86637891Ethyl (3-{3-[(3,3-diphenylpropyl)amino]propyl}phenoxy)acetateYield 40.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl [3-(3-iodopropyl)phenoxy]acetate (2.5 g) in DMF (50 mL) was added (3,3-diphenylpropyl)amine (1.7 g) at ambient temperature. The reaction mixture was stirred for 8 hours at the same temperature. The resulting mixture was diluted with EtOAc and washed successively with saturated NaHCO3 aqueous solution, water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:MeOH=100:0-95:5) to give ethyl (3-{3-[(3,3-diphenylpropyl)amino]propyl}phenoxy)acetate (1.25 g).

Workup

  1. washwashed successively with saturated NaHCO3 aqueous solution, water and brine
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (chloroform:MeOH=100:0-95:5)

Sources & evidence

ORD record
ord-8483082847264535990166b728b9bbac
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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