Benzaldehyde → HCID 57820079, compound

HRID 1714169Notes

Reaction equation

HRID 1714169 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[O:10])=[CH:4][CH:3]=1.[CH:31](=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:22]([CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:11]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:16][CH:17]=3)[C:9]2=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 24436Sodium SulfateHCID 57819988HCID 57819988, compound

Product 1

HCID 57820079HCID 57820079, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-bromo-phenyl)-2-(2-morpholin-4-yl-ethylamino)-N-(4-trifluoromethyl-phenyl)-acetamide (2.90 g, 6.00 mmol) in anhydrous MeOH (20 mL) was added benzaldehyde (633 mg, 6.00 mmol), followed by para-toluenesulfonic acid (229 mg, 1.20 mmol) and sodium sulfate (8.98 g, 63.2 mmol). The reaction was refluxed overnight, filtered, and directly purified by flash column chromatography eluting with ethyl acetate: petroleum ether gradient (10%-25%) to afford the product as a yellow solid (2.38 g, 69.2%).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. filtrationfiltered
  3. customdirectly purified by flash column chromatography
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-ee786dcb35ca488fb8b7da70827634c4
Source dataset
uspto-grants-2010_09
Patent number
US07795315B2

Reaction notes

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