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

HRID 1356462Notes

Reaction equation

HRID 1356462 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].OC1C=CC=CN=1>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 66053N,N-DimethylethylenediamineHCID 18508368Methyl 4-(4-biphenylylmethoxy)phenylacetateHCID 178516071HCID 178516071, compound

Product 1

HCID 99102684-(4-Biphenylylmethoxy)phenyl-N-[2-(N,N-dimethylamino)ethyl]acetamideYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A suspension of methyl 4-(4-biphenylylmethoxy)phenylacetate (2.00 g), N,N-dimethylethylenediamine (1.60 g), 2-hydroxypyridine (573 mg) in methanol (4.0 ml) was heated under reflux under nitrogen for 16 hr and cooled until the temperature of the reaction mixture reached to 60±2° C., to which methanol (8.0 ml) was added. The reaction mixture was heated under reflux for additional one hr and cooled to room temperature. The precipitate was collected by filtration and washed with methanol (4.0 ml to obtain the titled compound (2.18 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen for 16 hr
  3. temperaturecooled until the temperature of the reaction mixture
  4. additionwas added
  5. temperatureThe reaction mixture was heated
  6. temperatureunder reflux for additional one hr
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with methanol (4.0 ml

Sources & evidence

ORD record
ord-7c55b8e3a7dc4eae93244fc356c1ee9b
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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