Imidazole → 4-(4-Biphenylylmethoxy)phenyl-N-[2-(N,N-dimethylamino)ethyl]acetamide

HRID 1356463Notes

Reaction equation

HRID 1356463 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16](OC)=[O:17])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][NH2:30].N1C=CN=C1>CO>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=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:30][CH2:29][CH2:28][N:27]([CH3:31])[CH3:26])=[O:17])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 66053N,N-DimethylethylenediamineHCID 18508368Methyl 4-(4-biphenylylmethoxy)phenylacetate

Product 1

HCID 99102684-(4-Biphenylylmethoxy)phenyl-N-[2-(N,N-dimethylamino)ethyl]acetamideYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A suspension of methyl 4-(4-biphenylylmethoxy)phenylacetate (1.00 g), N,N-dimethylethylenediamine (0.80 g), and imidazole (205 mg) in methanol (2.0 ml) was heated under reflux under nitrogen for 30 min and cooled until the temperature of the reaction mixture reached to 60±2° C. Methanol (4.0 ml) was added to the reaction mixture, which was heated under reflux for additional one hr and cooled to room temperature. The precipitate was collected by filtration and washed with methanol (2.0 ml) to obtain the titled compound (1.03 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen for 30 min
  3. temperaturecooled until the temperature of the reaction mixture
  4. customreached to 60±2° C
  5. temperaturewas heated
  6. temperatureunder reflux for additional one hr
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with methanol (2.0 ml)

Sources & evidence

ORD record
ord-21691dadf78d4e46a7065ef17ec8c5cf
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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