4-Fluorobenzaldehyde → HCID 58531372, compound

HRID 1889703Notes

Reaction equation

HRID 1889703 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH2:16])[CH:10]=2)=[CH:5][CH:4]=1.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CC(O)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][CH2:22][C:21]3[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=3)[CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 179988491-(4'-Chloro[1,1'-biphenyl]-3-yl)methanamine--hydrogen chloride (1/1)

Product 1

HCID 58531372HCID 58531372, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4′-chlorobiphenyl-3-yl)methanamine HCl salt (Chem-Impex International, Inc., 0.6 g, 2.36 mmol) in CH2Cl2 (6 mL) and 2-propanol (6.00 mL) was added 4-fluorobenzaldehyde (0.28 mL, 2.60 mmol). The resulting reaction mixture was stirred at rt for 1 h. and sodium triacetoxyborohydride (0.75 g, 3.54 mmol) was added under N2. After stirring at rt for 3 h, the reaction mixture was quenched with saturated aqueous NaHCO3, stirred for 10 minutes and concentrated in vacuo. The residue was diluted with ethyl acetate and saturated aqueous NaHCO3 solution. The organic layer was separated, washed with brine, dried over MgSO4, filtered and the filtrate solution was concentrated in vacuo. The residue was purified by flash silica gel chromatography eluting with 0-10% ethyl acetate in CH2Cl2 to afford the desired compound (0.63 g, 73%) as a colorless oil. 1H NMR (CDCl3) δ 7.62-7.41 (m, 6H), 7.37-7.32 (m, 3H), 7.09-7.01 (m, 3H), 3.92 (s, 2H), 3.83 (s, 2H). MS (ESI): 326.0 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. stirringAfter stirring at rt for 3 h
  3. customthe reaction mixture was quenched with saturated aqueous NaHCO3
  4. stirringstirred for 10 minutes
  5. concentrationconcentrated in vacuo
  6. additionThe residue was diluted with ethyl acetate and saturated aqueous NaHCO3 solution
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationthe filtrate solution was concentrated in vacuo
  12. customThe residue was purified by flash silica gel chromatography
  13. washeluting with 0-10% ethyl acetate in CH2Cl2

Sources & evidence

ORD record
ord-b8910cac4bf747a8a95fc6ce6a837f66
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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