Benzylamine → HCID 178488570, compound

HRID 493496Notes

Reaction equation

HRID 493496 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=O)=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH2:18](/[N:25]=[CH:16]\[C:13]1[CH:14]=[CH:15][C:10]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Br:1])[CH:3]=2)=[CH:11][CH:12]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 576816103'-Bromo-4'-methoxy-1,1'-biphenyl-4-carbaldehyde

Product 1

HCID 178488570HCID 178488570, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3′-bromo-4′-methoxy-1,1′-biphenyl-4-carbaldehyde (19.4 g, 69 mmol), prepared in step 3 of Example 6, benzylamine (38 mL, 345 mmol) and 60 g of anhydrous MgSO4 in 400 mL of methylene chloride was stirred under nitrogen at room temperature for 18 h. The reaction was filtered and the filtrate concentrated under reduced pressure to give an off-white solid. The solid was triturated with hexane and dried under reduced pressure to give N-benzyl-N-[(1Z)-(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methylidene]amine (23.6 g, 88%) as an off-white solid, MS KESI) m/z 380 [M+H]+. Elemental analysis for C21H18BrNO: Calc'd: C, 66.33; H, 4.77; N, 3.68; Found: C, 63.22; H, 4.85; N, 4.17

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto give an off-white solid
  4. customThe solid was triturated with hexane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-5a526a0f595d4ea1a2feffe915905b36
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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