1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(4-Biphenylylmethoxy)phenyl-N-[2-(N,N-dimethylamino)ethyl]acetamide

HRID 1356465Notes

Reaction equation

HRID 1356465 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16](O)=[O:17])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:46][N:47]([CH3:51])[CH2:48][CH2:49][NH2:50]>C1COCC1>[C:1]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:50][CH2:49][CH2:48][N:47]([CH3:51])[CH3:46])=[O:17])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 17817500HCID 17817500, compound

Product 1

HCID 99102684-(4-Biphenylylmethoxy)phenyl-N-[2-(N,N-dimethylamino)ethyl]acetamideYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-biphenylylmethoxy)phenylacetic acid (0.6 g) in THF (30 ml) were added WSC (0.4 g) and HOBt (0.3 g). N,N-Dimethylethylenediamine (0.2 g) was added to the reaction mixture. After stirring at room temperature for 18 hr, the reaction mixture was poured onto water and extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated in vacuo. The residue was recrystallized from ethyl acetate/ethanol to obtain the titled compound (0.3 g).

Workup

  1. additionthe reaction mixture was poured onto water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-b16297c3b0974842b3962ff215fda952
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

Loading…