Benzhydrylamine → HCID 178491052, compound

HRID 509187Notes

Reaction equation

HRID 509187 reaction equation
[C:1]1([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20](/[CH:21]=[N:8]/[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 10340Sodium CarbonateHCID 312444-Methoxybenzaldehyde

Product 1

HCID 178491052HCID 178491052, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of diphenylmethanamine (3.00 g, 16.4 mmol) in methanol (80 mL) was added 4-methoxybenzaldehyde (2.45 g, 18.0 mmol) and sodium carbonate (2.60 g, 24.6 mmol). The reaction mixture was stirred at room temperature for 16 h prior to removal of all solvents under vacuum. The residue was then diluted with ethyl acetate, washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford compound 39 as a white solid (3.62 g, 73%). LRMS (ESI): (calc.) 301.4 (found) 302.4 (MH)+.

Workup

  1. customto removal of all solvents under vacuum
  2. additionThe residue was then diluted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-608fea230c204f63994022fddcbf34fd
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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