Formaldehyde → 4-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-dimethylaminomethylphenyl)benzamide

HRID 323150

Reaction equation

HRID 323150 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:35]=[CH:34][C:20]([C:21]([N:23]([CH3:33])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH2:30][NH:31][CH3:32])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C=O.[C:38]([BH3-])#N.[Na+]>CO.C(O)(=O)C.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:33])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH2:30][N:31]([CH3:38])[CH3:32])=[O:22])=[CH:34][CH:35]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 220108454-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-methylaminomethylphenyl)benzamide

Product 1

HCID 220107924-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-dimethylaminomethylphenyl)benzamideYield 41%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-methylaminomethylphenyl)benzamide (154 mg) in a mixture of methanol (10 ml) and acetic acid (0.5 ml) were added aqueous formaldehyde (0.2 ml) and sodium cyanoborohydride (20.9 mg) and the solution was stirred at ambient temperature for 4 hours. The mixture was diluted with chloroform and the solution was washed with saturated aqueous sodium hydrogen carbonate and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give crude oil. The oil was purified by silica gel column (10 g, 2% methanol in chloroform) and the product was solidified with diethyl ether to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-dimethylaminomethylphenyl)benzamide (65 mg) as a white powder.

Workup

  1. washthe solution was washed with saturated aqueous sodium hydrogen carbonate and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customto give crude oil
  5. customThe oil was purified by silica gel column (10 g, 2% methanol in chloroform)

Sources & evidence

ORD record
ord-7f02cd0acf134e0d9b4a99198696aa62
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Linked notes

Loading…