Dimethylamine → HCID 19043749, compound

HRID 2255285Notes

Reaction equation

HRID 2255285 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([N:17]([O:19][CH3:20])[CH3:18])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:21][NH:22][CH3:23]>C(O)C>[CH3:21][N:22]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([N:17]([O:19][CH3:20])[CH3:18])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH3:23]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 19742092HCID 19742092, compound

Product 1

HCID 19043749HCID 19043749, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.95 g of 4'-bromomethyl-N-methoxy-N-methyl-4-biphenylcarboxamide was treated with 20 mL of a 33% solution of dimethylamine in ethanol, stirred at room temperature for 24 hours, the reaction mixture was evaporated, the residue was dissolved in 50 mL of ethyl acetate and washed with 50 mL of sodium hydroxide solution and with 50 mL of a saturated sodium chloride solution. The organic phases were dried over magnesium sulphate and evaporated. The crude product was chromatographed on 100 mL of silica gel with methylene chloride/methanol 9:1. There was obtained 1.16 g (52%) of 4'-[(dimethylamino)methyl]-N-methoxy-N-methyl-4-biphenylcarboxamide as a colorless solid with a m.p. of 42°-43° C.

Workup

  1. customthe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in 50 mL of ethyl acetate
  3. washwashed with 50 mL of sodium hydroxide solution and with 50 mL of a saturated sodium chloride solution
  4. dry with materialThe organic phases were dried over magnesium sulphate
  5. customevaporated
  6. customThe crude product was chromatographed on 100 mL of silica gel with methylene chloride/methanol 9:1

Sources & evidence

ORD record
ord-f0a823c781794a7082799cf8dddd200e
Source dataset
uspto-grants-1993_08
Patent number
US05239084

Reaction notes

Loading…